Title of Invention

REAGENT FOR ORGANIC SYNTHESIS

Abstract A reagent for organic syntheses with which a chemical reaction can be conducted in a liquid phase and unnecessary compound(s) can be easily separated at low cost from the liquid phase after completion of the reaction. The reagent for organic syntheses reversibly changes from a liquid-phase state to a solid-phase state with changes in solution composition and/or solution temperature, and is for use in organic synthesis reactions. This reagent for organic syntheses facilitates process developments. With the reagent, researches on and developments of, e.g., medicines through, e.g., compound library syntheses, etc. can be accelerated. It can hence contribute to a technical innovation in the biochemical industry and chemical industry.
Full Text REAGENT FOR ORGANIC SYNTHESIS AND METHOD OF ORGANIC SYNTHESIS
REACTION WITH THE REAGENT
TECHNICAL FIELD
The present invention relates to a reagent for organic
synthesis and a method of organic synthesis reaction using
this reagent, and in more detail, it relates to a reagent for
organic synthesis which is a compound which rapidly changes
from a liquid phase state to a solid phase state due to a
change in solution composition and/or solution temperature,
which is provided as a compound acting as a reaction substrate
or a catalyst in an organic synthesis reaction, or which is
provided as a compound which bonds to unreacted compounds or
byproducts in an organic synthesis reaction, which can be eas-
ily removed from the reaction system after the; reaction; and
to a method of organic synthesis using this reagent.
BACKGROUND ART
In chemical reaction processes, methods of separating as a
solid a specified component dissolved in a liquid are widely
used. This is because, by solidifying (crystallizing) only
the specified component, separation and/or purification after
the reaction are simplified. In particular, recently, in suc-
cessive multistage synthesis such as compound library synthe-
sis and the like used in the research and development of phar-
maceuticals, after the completion of each reaction, by solidi-
fying (crystallizing) the unnecessary compounds, the removal

of the solidified (crystallized) substances becomes easy, and
it is possible to prevent the processes from becoming compli-
cated.
The solidification (crystallization) of specified compo-
nents dissolved in a solution in this way is implemented by
satisfying defined conditions in the relationship with chemi-
cal properties and physical properties of the compounds, and
with the solvent.
However, the conditions for solidification (crystalliza-
tion), in many cases, must be found by experience based on
trial and error. Especially, in successive multistage synthe-
sis, because it is necessary to consider the solidification
(crystallization) conditions based on the characteristic prop-
erties of the compounds synthesized in each of the stages,
process development is very expensive and time consuming.
In order to solve such problems, in the prior art, there
was known a means of using a chemically modified reagent on
polystyrene or silica, and separating the liquid including the
products, and the reagents, by filtration after the reaction.
With these reagents, it is possible to easily separate unre-
acted compounds added in excess, byproducts, and catalysts, in
an organic synthesis reaction or the like, without complicated
separation processes.
Further, Patent Document 1 discloses a method for practic-
ing a nucleophilic substitution reaction (Mitsunobu reaction)
of an alcohol for producing a desired product, including a
step of reacting an alcohol and a nucleophilic reagent with an

azodicarboxylate and a phosphine, wherein at least one of the
azodicarboxylate and phosphine include at least one fluorous
tag (a retention group of a highly fluorinated alkyl group or
the like). Here, for example, fluorous solvents including
perfluorocarbon or the like, will be present as a third phase
without mixing with organic solvents or water, and have the
characteristic of dissolving compounds having a fluorous tag.
Because of this, by adding a fluorous solvent to a uniform re-
action phase, it is possible to easily separate a compound
which must be separated from the product, and which has a flu-
orous tag.
Further, by using a fluorous carrier which selectively
bonds to a fluorous tag, it is possible to easily separate a
compound having a fluorous tag by solid-liquid.extraction.
Patent Document 1: Japanese Publication No. 2005-508890 of
PCT Application.
DISCLOSURE OF THE INVENTION
Problems to be Solved by the Invention
However, in the case of utilizing a reaction using a chem-
ically modified reagent on polystyrene or silica, for the
reagent carried on the polystyrene or silica, the reaction
point is only at the solid liquid interface, thus the reactiv-
ity is often low. Further, there was the problem that it was
not possible to use this method in many synthesis reactions
where a product is produced by the reaction from sterically
plural directions, two or more reagents, because the reaction

was carried out on a solid surface.
Further, in the method disclosed in Patent Document 1, in
the case of using a fluorous solvent when separating a com-
pound having a fluorous tag, there was the problem that the
costs of the reaction could not be kept low because fluorous
solvents are expensive. Further, in the case of using a fluo-
rous carrier in the separation of a compound having a fluorous
tag, in addition to using an expensive fluorinated silica gel
or the like, the separation operation is complex and cannot be
easily used.
The present invention was made in view of the above prob-
lems, and has the objective of providing a reagent for organic
synthesis and a method of organic synthesis reaction using the
reagent, whereby a chemical reaction can be carried cut in a
liquid phase, and further, the separation of the unnecessary
compounds from the liquid phase after the completion of the
reaction can be carried out easily and also at low cost.
Means for Solving the Problems
The present inventors have carried out diligent research
in order to solve the above problems. As a result, they ar-
rived at and completed the present invention, discovering that
by using a reagent for organic synthesis including an aromatic
group having a specified hydrophobic group, and having a prop-
erty of reversibly changing from a liquid phase state to a
solid phase state according to changes in the solution compo-
sition and/or the solution temperature, it is possible to car-
ry out the separation of unnecessary compounds from the liquid

phase after the completion of the reaction, easily and fur-
thermore, at low cost.
Specifically, the present invention provides the follow-
ing.
The first aspect of the invention provides a reagent for
organic synthesis which can be used for organic synthesis re-
actions, shown in the below Chemical Formula (1), having a
property of reversibly changing from a liquid phase state to a
solid phase state according to changes in solution composition
and/or solution temperature.

(In the formula, Rx to R5 may be the same or different, and
represent hydrogen, halogen, or alkyl group with a carbon num-
ber of 1 to 30 which may have a substituent group, alkoxyl
group with a carbon number of 1 to 30 which may have a sub-
stituent group, aryl group with a carbon number of 1 to 30
which may have a substituent group, acyl group with a carbon
number of 1 to 30 which may have a substituent group,
thioalkyl group with a carbon number of 1 to 30 which may have
a substituent group, dialkylamino group with a carbon number
of 1 to 30 which may have a substituent group, nitro group or
amino group, and at least two of R1 to R5 are alkyl group with
a carbon number of 18 to 30 which may have a substituent

group, alkoxyl group with a carbon number of 18 to 30 which
may have a substituent group, acyl group with a carbon number
of 18 to 30 which may have a substituent group, thioalkyl
group with a carbon number of 18 to 30 which may have a sub-
stituent group, or dialkylamino group with a carbon number of
18 to 30 which may have a substituent group. Further, in the
formula, X represents a reagent active site having one or more
atoms selected from the group consisting of a carbon atom,
oxygen atom, sulfur atom, and nitrogen atom.)
According to the reagent for organic synthesis according
to the first aspect, in addition to having a reagent active
site having one or more atoms selected from the group consist-
ing of carbon, oxygen, sulfur, or nitrogen atoms, it also has,
as substituent groups on the. aromatic ring, at least two of:
alkyl group with a carbon number of 18 to 30 which may have a
substituent group, alkoxyl group with a carbon number of 18 to
30 which may have a substituent group, acyl group with a car-
bon number of 18 to 30 which may have a substituent group, a
thioalkyl group with a carbon number of 18 to 30 which may
have a substituent group, or a dialkylamino group with a car-
bon number of 18 to 30 which may have a substituent group.
Because of this, the reagent for organic synthesis can be dis-
solved uniformly with high concentration in many organic sol-
vents, and it can react with a high degree of reactivity with
other compounds in many organic solvents.
Further, the reagent for organic synthesis according to
the first aspect can also be used mainly as a nucleophilic

scavenger, electrophilic scavenger, synthesis building block,
reaction accelerator, condensation agent, or metal ligand.
Namely, it can be used in a wide range of applications, as a
reaction substance for unnecessary ,substances such as byprod-
ucts, catalysts, and unreacted reaction substrate and the
like, as a reaction substrate in an organic synthesis reac-
tion, and as a catalyst or reaction accelerator in an organic
synthesis reaction, and in addition, it has the property of
reversibly changing from a liquid phase state to a solid phase
state according to changes in solution composition and/or so-
lution temperature, and thus can be easily separated from the
reaction system by solidification after the reaction.
In this way, any compounds added to a reaction system, and
byproducts generated in the reaction system, can be easily
separated from the reaction system, or a specified reaction
substrate or reaction accelerator can be added to the reaction
system as a compound which can be easily separated later, and
can be easily separated from the reaction system after the
completion of the reaction.
Further, in a reaction using the reagent for organic syn-
thesis of the first aspect, the organic synthesis reaction can
be carried out at low cost without using particularly expen-
sive reagents.
Here, the "reagent for organic synthesis" indicates all
reagents used for carrying out organic synthesis reactions, or
processes after the reaction, and includes reaction sub-
strates, reaction accelerators, and synthesis building blocks,

and the like. The reagent for organic synthesis according to
the present invention is not particularly limited in terms of
the amount used, and can be used in any case such as the case
of use in large industrial quantities, or the case of use in
small quantities for testing, research or the like. In the
present invention, in particular, the compound has a structure
such as that shown in Chemical Formula (1).
Further, the "reagent for organic synthesis" of the
present invention has a "hydrophobic carrier group" as a por-
tion thereof. In the present invention, "hydrophobic carrier
group" indicates, in the compound (1), a site having a hy-
drophobic group, and specifically, in the Chemical Formula
(1), indicates a portion excluding the reagent active portion
which is X.
Further, "nucleophilic scavenger" indicates a compound
which can bond to excess electrophilic reagents remaining un-
reacted with other reaction substrate substances among elec-
trophilic reagents used a chemical reaction, and to compounds
having electrophilicity which are produced as reaction byprod-
ucts, and further to unreacted reaction substrate.
The term "electrophilic scavenger" indicates a compound
which can bond to excess nucleophilic reagents remaining unre-
acted with other reaction substrate substances among nucle-
ophilic reagents used in a chemical reaction, and to compounds
having nucleophilicity which are generated as reaction byprod-
ucts, and further to unreacted reaction substrate.
The term "synthesis building block" indicates an interme-

diate provided for the organic synthesis reaction of the de-
sired compound in the present invention, and indicates a gen-
eral term for a compound which can impart an arbitrary reagent
activity to a reaction substrate by introducing a specified
functional group via chemical bonding in an arbitrary reaction
substrate.
The term "condensation agent" indicates a compound which
acts to accelerate a dehydration condensation reaction by ac-
celerating the elimination of active hydrogen and hydroxyl
groups from a reaction substrate in a dehydration condensation
reaction such as an ester synthesis reaction, amide synthesis
reaction, ether synthesis reaction or the like.
The term "metal ligand" indicates a compound having an
atomic group which can coordinate and bond to a metal ion
added as a catalyst or reaction accelerator in an organic syn-
thesis reaction.
Further, "reaction accelerator" indicates a compound which
can accelerate an organic synthesis reaction by addition to a
reaction system, and for example, acids, bases, catalysts and
the like can be mentioned.
The second aspect of the invention provides a reagent for
organic synthesis according to the first aspect, characterized
in that, in Chemical Formula (1), X is a functional group
shown by (A) to (M), or (A') to (M') below.





(In the formulas (A) to (M), Y is an ester bond, ether bond,
amide bond, thioester bond, sulfide bond, urea bond, carbamate
bond, or carbonate bond, or an alkylene group with a carbon
number of 1 to 10 which may have such bonds. Further, in for-

mulas (M) and (M'), m and n are independently 0 or 1, Za is a
chlorine atom or a bromine atom, Zb is a hydroxyl group, chlo-
rine atom, or a bromine atom.)
Here, a "carbamate bond" is the chemical bond shown in
Chemical Formula (N).

Further, a "carbonate bond" is the chemical bond shown in
Chemical Formula (0).

The reagent for organic synthesis of the second aspect can
be used for the following applications. Namely, in the case
that among the compounds (1) indicated in the second aspect, X
is reagent active site shown by the Chemical Formula (A) to
(C) or (A') to (C), because it has a reaction center having
nucleophilicity, such as a thiol group, amino group, or the
like, it can be used as a nucleophilic scavenger.
Further, in the case that among the compounds (1) shown in
the second aspect, X is a reagent active site indicated by the
Chemical Formulas (D) to (H), or (D') to (H'), because it has
a reaction center having electrophilicity, such as a carbonyl
carbon atom, or the like, it can be used as an electrophilic
scavenger. Further, also in the case that among the compounds
(1), X is a reagent active site shown by the Chemical Formulas

(M), or (M'), because the carbon atom to which a hydroxyl
group is bonded, and the carbon atom to which to a halogen
atom, not directly bonded to a benzene ring, is bonded have
electrophilicity, it can be used as an electrophilic scav-
enger.
Moreover, in the case that among the compounds (1) indi-
cated in the second aspect, X is a reagent active site shown
by the Chemical Formulas (A) to (H), or (A1) to (H1), because
structural changes for a compound having arbitrary reagent ac-
tivity are possible via a sulfide bond, thioester bond, amino
bond, amide bond, carbamate bond, urea bond, carbonate bond,
ether bond, or ester bond, it can also be used as a synthesis
building block.
In the case that among the compounds (1) indicated in the
second aspect, X is a reagent active site shown by the Chemi-
cal Formulas (I), (J), (I') or (J'), because an amino group or
the like shows strong basicity, it can be used as a reaction
accelerator as a strong base. Namely, these compounds, as
strong bases, by capturing active hydrogen of one portion of
the reaction substrate, can be used as reaction accelerators
for nucleophilic reactions, deprotecting reactions, esterifi-
cation reactions of carboxylic acids, alkylation reactions of
active methylenes, alkylation reactions of amines, alkylation
reactions of phenols, alkylation reactions of thiols, and the
like.
In the case that among the compounds (1) indicated in the
second aspect, X is a reagent active site shown by the Chemi-

cal Formulas (K), or (K'), the unbonded electron pair of the
phosphorous atom is donated to a metal atom, and in addition,
an electron pair is back-donated from the metal atom to the n
orbital of the tertiary phosphine. Because of this, these
compounds can form strong coordination bonds with metal atoms.
Further, in the case that among the compounds (1) indicat-
ed in the second aspect, X is a reagent active site shown by
the Chemical Formulas (K), (L), (K'), or (L'), because (K) or
(K') act in the same way as triphenylphosphine, and further,
because (L) or (L') act in the same way as diethyl azodicar-
boxylate, these can be used as condensation agents for many
condensation reactions publicly known as Mitsunobu reactions.
The third aspect of the invention provides a reagent for
organic synthesis according to the first or second aspect,
wherein in the Chemical Formula (1), R2 and R4 are a docosyloxy
group (C22H45O-) , and Rl, R3 and R5 are hydrogen.
Because the reagent for organic synthesis according to the
third aspect has two docosyloxy groups, it can be dissolved
uniformly at high concentration in many organic solvents, and
it can react with a high degree of reactivity with other com-
pounds in many organic solvents.
The fourth aspect of the invention provides a reagent for
organic synthesis according to the third aspect, wherein in
the Chemical Formula (1), the reagent active site X is a func-
tional group shown by the formula (M) or (M').
The reagent for organic synthesis according to the fourth
aspect is, specifically, the compound shown by Chemical Formu-


(In Formula (2a), m and n are independently 0 or 1, Za is a
chlorine atom, or bromine atom, Zb is a hydroxyl group, chlo-
rine atom, or bromine atom.)
Because the reagent for organic synthesis according to the
fourth aspect has a hydroxyl group, chlorine atom, or bromine
atom, it can be used as an electrophilic scavenger. Further,
because the reagent for organic synthesis according to the
fourth aspect has two docosyloxy groups, it can.be dissolved
uniformly at high concentration in many organic solvents, and
it can react with a high degree of reactivity with other com-
pounds in many organic solvents.
The fifth aspect of the invention provides a reagent for
organic synthesis according to the first: aspect, wherein in
the Chemical Formula (1), the reagent active site X is a hy-
droxymethyl group, and R2 and R4 are a docosyloxy group
(C22H45O-) , and R1, R3 and R5 are hydrogen.
In other words, the invention according to the fifth as-
pect is a reagent for organic synthesis shown by the following
Chemical Formula (2) which can be used for organic synthesis.


Because the reagent for organic synthesis according to the
fifth aspect has a hydroxyl group, it can be used as an nucle-
ophilic scavenger. Further, because the reagent for organic
synthesis according to the fifth aspect has two docosyloxy
groups, it can be dissolved uniformly at high concentration in
many organic solvents, and it can react with a high degree of
reactivity with other compounds in many organic solvents.
The sixth aspect of the invention provides a method of or-
ganic synthesis reaction using the reagent for organic synthe-
sis according to any one of the first to fifth aspects, com-
prising a reaction step of carrying out a reaction wherein the
reagent for organic synthesis is dissolved in a reaction sys-
tem where the reagent active site X of Chemical Formula (1)
participates in the reaction, and after this, a separation
step of separating the reagent for organic synthesis and the
reacted reagent for organic synthesis.
Taking note of the reagent for organic synthesis disclosed
in the fifth aspect, the invention according to the sixth as-
pect is method of organic synthesis reaction using the reagent
for organic synthesis according to the fifth aspect, compris-
ing a reaction step of carrying out a reaction where the
reagent for organic synthesis is dissolved in a reaction sys-
tem where the hydroxyl group in Chemical Formula (2) partici-

pates in the reaction, and after this, a separation step of
separating the reagent for organic synthesis and the reacted
reagent for organic synthesis.
According to the method of organic synthesis reaction ac-
cording to the sixth aspect, in the reaction step, it is pos-
sible to carry out a chemical reaction for producing the de-
sired compound, using the reagent for organic synthesis ac-
cording to any one of the first to fifth aspects. Further,
because it is possible to separate, by the separation step,
byproducts having a hydrophobic carrier group of the reagent
for organic synthesis among the byproducts produced by the
chemical reaction, and the reagent, for organic synthesis added
to the reaction system in excess and remaining unreacted, it
is possible to easily carry out a procedure of separating oth-
er compounds from the desired compound.
Further, in the reaction step of the method of organic
synthesis reaction according to the sixth aspect, it is also
possible to add a reagent for organic synthesis in addition to
any chemical reaction for obtaining the desired compound, and
to react the reagent for organic synthesis with excess reac-
tion substrate added in excess to the reaction system and
byproducts.
Here, "method of organic synthesis reaction" indicates a
method for producing by an organic synthesis reaction a de-
sired compound, and in the present invention, in particular,
it indicates a method using the reagent for organic synthesis
disclosed in any of the first to fifth aspects. The method of

organic synthesis reaction of the present invention is not
particularly limited in the used amount of the reagent for or-
ganic synthesis, and can be carried out with any amount, such
as the case of using the reagent for organic synthesis in
large industrial amounts, or in the case of using small
amounts in testing and research.
Further, the separation step in the method of organic syn-
thesis reaction according to the sixth embodiment includes a
step of crystallizing and separating the reagent for organic
synthesis, and the reacted reagent for organic synthesis, by
means of changing the solution composition and/or by means of
changing the solution temperature. Namely, because the
reagent for organic synthesis disclosed in any one of the
first to fifth aspects reacts, sharply to changes in solvent
composition and/or solvent temperature, by using a means to
change the composition and/or the temperature of the solvent,
the reagent for organic synthesis or the reacted reagent for
organic synthesis can be crystallized, and the reagent for or-
ganic synthesis and the reagent for organic synthesis after
reaction can be easily crystallized and separated in a state
where the desired compound of the synthesis remains in the so-
lution.
As the means for changing the solution composition, for
example, the means of adding another solvent to the reaction
system, such as a poor solvent with respect to the reagent for
organic synthesis, or the means of concentrating the solvent
can be mentioned. As a means for changing the solution tern-

perature, for example, the means of cooling the solution can
be mentioned.
Effects of the Invention
According to the present invention, the reagent for organ-
ic synthesis can be uniformly dissolved in many organic sol-
vents, and thus can be reacted with a high degree of reactivi-
ty with other compounds. Further, after the reaction, it is
possible to choose from many separation methods such as a sol-
id liquid separation method by crystallizing the reagent for
organic synthesis, and the reacted reagent for organic synthe-
sis, or a liquid liquid extraction method by adding a separa-
tion solvent which is immiscible with the reaction solvent,
and partitioning the reagent for organic synthesis and the re-
acted reagent for organic synthesis into the separation sol-
vent. Because the separation conditions of these separation
methods can be uniformly determined based on the properties of
the reagent for organic synthesis, it is not necessary to con-
sider the separation conditions based on the characteristic
properties or the like of each organic synthesis reaction.
This not only simplifies process development, but also, for
example, makes it possible to accelerate the research and de-
velopment of pharmaceuticals and the like by compound library
synthesis and the like, and this can in turn contribute to
technical innovations in the biochemical industry and chemical
industry.
Further, organic synthesis reactions using the organic
synthesis reagent of the present invention do not use espe-

cially expensive compounds, and thus the organic synthesis re-
action can be carried out at low cost.
PREFERRED MODE FOR CARRYING OUT THE INVENTION
Embodiments of the invention are described in detail be-
low. These embodiments do not in any way limit the reagent
for organic synthesis or the method of organic synthesis reac-
tion using this reagent of the present invention, and appro-
priate modifications can be made within the scope of the ob-
jectives of the present invention.
Reagent for Organic Synthesis
The reagent for organic synthesis according to the present
embodiment is shown by Chemical Formula (1) where R1 to R5 may
be the same or different, and represent a hydrogen, halogen,
alkyl group, alkoxyl group, aryl group, acyl group, thioalkyl
group, or dialkylamino group with a carbon number of 1 to 30
which may have a substituent group; nitro group, or amino
group, and at least two of R1 to R5 are alkyl group, alkoxyl
group, acyl group, thioalkyl group, or dialkylamino group with
a carbon number of 18 to 30 which may have a substituent
group. Further, in the formula, X represents a reagent active
site having at least one atom selected from the group consist-
ing of carbon, oxygen, sulfur or nitrogen atom.


Because the above compound has at least two hydrophobic
groups selected from the group consisting of alkyl group,
alkoxyl group, acyl group, or thioalkyl group with a carbon
number of 18 to 30 which may have a substituent group, it can
show sufficient hydrophobicity, and can dissolve in a wide
range of organic solvents, and further, a compound where the
3-position and 5-position with respect to X (R2 and R4) are
substituted with an alkoxyl group with a carbon number of 18
to 30 is also stable with respect to acid treatment, and is
especially suitable for the reagent for organic synthesis of
the present invention.
Reagent Active Site
In the above Chemical Formula (1), X indicates a reagent
active site having at least one atom selected from the group
consisting of carbon, oxygen, sulfur, and nitrogen atom.
Here, X may also have a structure indicated by the following
Chemical Formulas (A) to (M), or (A') to (M'). Here, Y is an
ester bond, ether bond, amide bond, amino bond, thioester
bond, sulfide bond, urea bond, carbamate bond or a carbonate
bond, or an alkylene group with a carbon number of 1 to 10
which may have one of these bonds. Further, in Formulas (M)
and (M'), m and n are independently 0 or 1, Za is a chlorine

atom or bromine atom, and Zb is a hydroxyl group, chlorine
atom, or bromine atom.



Further, in the reagent for organic synthesis of the
present embodiment, a compound where R2 and R4 are docosyloxy
groups (C22H45O-), and R1, R3 and R5 are hydrogen is preferable.
Furthermore, the reagent for organic synthesis of the

present embodiment may be a compound shown by the following
Chemical Formula (2).

Namely, the compound shown by the Chemical Formula (2) is
a reagent for organic synthesis shown by the Chemical Formula
(1), wherein in the Chemical Formula (1), X is a hydroxymethyl
group, R2 and R4 are docosyloxy (C22H45O-) , R1, R3 and R5 are hy-
drogen.
Here, the compound shown by the Chemical Formula (2) has a
hydroxyl group, and because it shows nucleophilicity, it can
be used as a nucleophilic scavenger.
Manufacturing Method of the Reagent for Organic Synthesis
The manufacturing method of the reagent for organic syn-
thesis indicated in the above formula is not particularly lim-
ited, but it can generally be synthesized by various reactions
such as the following.
A compound having a plurality of phenolic hydroxyl groups
such as methyl gallic acid, and a long chain brominated alkyl
are reacted in N,N-dimethylformamide, under basic conditions,
to yield an aromatic compound having an alkoxy group. Next,
an ester site is converted to the other substituting group to
induce the desired compound by a functional group substitution
by a publicly known means, or the aromatic compound is combine

to a specially prepared reagent active site in an arbitrary
bounded form to manufacture the reagent of the present embodi-
ment .
Method of Organic Synthesis Reaction
The reagent for organic synthesis of the present embodi-
ment can be used by the same method of use as the reagent used
in the liquid phase organic synthesis reactions of the prior
art which do not have a hydrophobic carrier group. Namely, in
a state wherein the reaction substrate to be reacted is dis-
solved or dispersed in a solvent, a reagent for organic syn-
thesis having a hydrophobic carrier group is added, and a re-
action is carried out. Here, as the solvent used in the reac-
tion system, it is possible to use a general organic solvent
in the reaction, but because the reactivity is increased as
the solubility of the reagent for organic synthesis in the
solvent increases, it is preferable to select a solvent for
which the solubility of the reagent for organic synthesis is
high. Specifically, tetrahydrofuran, dichloromethane, di-
ethylether, hexane, cyclohexane, N,N-dimethylformamide and the
like are preferable, but it is not particularly limited to
this. To confirm the progress of the reaction, the same meth-
ods used for general liquid phase organic synthesis reactions
can be applied. Namely, thin layer silica gel chromatography,
high speed liquid chromatography, and the like can be used to
track the reaction.
Reaction Step
In the reaction step, by reacting a specified reaction

substrate and the reagent for organic synthesis, or by using
the reagent for organic synthesis as a reaction accelerator in
a specified chemical reaction, it is possible to obtain the
desired compound. Further, it is possible to carry out an ar-
bitrary chemical reaction for obtaining the desired compound,
and reacting residual reaction substrate added in excess to
the reaction system, and byproducts, with the reagent for or-
ganic synthesis.
Use of the Reagent for Organic Synthesis as a Synthesis Build-
ing Block
In the case of using the reagent for organic synthesis as
a synthesis building block, for example, consideration can be
given to using the reagent for organic synthesis as a reaction
substrate in a nucleophilic addition reaction, nucleophilic
substitution reaction, dehydration condensation reaction, and
the like. As a reagent for organic synthesis reaction which
can be used in such a reaction, there is no particular limita-
tion, and for example, in the reagent for organic synthesis
shown in Chemical Formula (1), a reagent for organic synthesis
where X is a reagent active site shown by (A) to (H) or (A')
to (H1) can be mentioned. As the solvent used for the reac-
tion, any solvent which can be ordinarily used for these reac-
tions can be used, and in the present embodiment, from the
point of solubility of the reagent for organic synthesis hav-
ing a hydrophobic carrier group, it is possible to use
tetrahydrofuran, dichloromethane, cyclohexane/N,N-dimethylfor-
mamide mixed solvent and the like.

Use or the Reagent for Organic Synthesis as a Reaction Accel-
erator
The reagent for organic synthesis of the present embodi-
ment can be used as a reaction accelerator. The effect as a
reaction accelerator depends on the properties of the reagent
active site of the reagent for organic synthesis, for example,
the degree of acidity and basicity, the catalytic activity and
the like. A reagent active site having such properties can be
introduced on a hydrophobic carrier group by using a synthesis
building block.
There is no particular limitation on the reagent for or-
ganic synthesis which can be used as a reaction accelerator,
and for example, in the reagent for organic synthesis shown by
Chemical Formula (1), a reagent for organic synthesis where X
is a reagent active site shown by (I), (J), (I') or (J') can
be mentioned. These reagents for organic synthesis show
strong basicity, and by scavenging active hydrogens of the re-
action substrate, can accelerate nucleophilic reactions, de-
protecting reactions, esterification reactions of carboxylic
acids, alkylation reactions of active methyl, alkylation reac-
tions of secondary amines, alkylation reactions of phenols,
and alkylation reactions of thiols.
Acceleration of Deprotecting Reactions
A reagent for organic synthesis having strong basicity can
be used, for example, for the deprotecting reaction of an Fmoc
group (9-fluorenylmethoxycarbonyl group), known as a protect-
ing group of amino groups, and the like, but it is not partic-

ularly limited to these reactions. As the solvent used for
the reaction, any one which can be ordinarily used for such
reactions can be used, and in the present embodiment, from the
point of solubility of the reagent for organic synthesis hav-
ing a hydrophobic carrier group, it is possible to use
tetrahydrofuran, dichloromethane, cyclohexane/N,N-dimethylfor-
mamide mixed solvent and the like.
The added amount of the reagent for organic synthesis used
in the reaction can be appropriately set by one skilled in the
art in consideration of the solubility of the reagent for or-
ganic synthesis in the used solvent, the equilibrium constant
of the acid-base equilibrium of the basic groups, the reaction
stoichiometry, and the like, and generally, it is preferable
to add one to five, times the theoretically required amount.
Further, a reagent for organic synthesis having a strong
basicity, in the same was as its use as an accelerator or a
deprotecting reaction, can be used as an accelerator of a nu-
cleophilic reaction, deprotecting reaction, esterification re-
action of a carboxylic acid, alkylation reaction of an active
methylene, alkylation reaction of an amine, alkylation reac-
tion of a phenol, alkylation reaction of a thiol, and the
like. In these cases, it is possible to use the same solvent
as the solvent used for a deprotecting reaction, and further,
it is possible to accelerate the reaction by adding the
reagent for organic synthesis in an amount which is the same
as that of the reagent for organic synthesis used to acceler-
ate deprotecting reactions.

Use of the Reagent for Organic Synthesis as a Condensation
Agent
The reagent for organic synthesis of the present embodi-
ment can be used as a condensation agent. For example, the
reagent for organic synthesis can be used as condensation
agent replacing the triphenylphosphine and diethyl azodicar-
boxylate required in the dehydration condensation reaction
publicly known as the Mitsunobu reaction. As such a reagent
for organic synthesis, for example, in the reagent for organic
synthesis shown in Chemical Formula (1), a reagent for organic
synthesis where X is a reagent active site shown by (K), (L),
(K'), or (L') can be mentioned.
The dehydration condensation reaction which can be used in
the present embodiment is not particularly limited, and for
example, ester synthesis reactions, amide synthesis reactions
and ether synthesis reactions can be mentioned. The solvent
used for the reaction is not particularly limited if it is a
solvent which can be ordinarily used for such reactions, and
in the present embodiment, from the point of solubility of the
reagent for organic synthesis having a hydrophobic carrier
group, it is possible to use tetrahydrofuran, dichloromethane,
cyclohexane/N,N-dimethylformamide mixed solvent and the like.
The added amount of the reagent for organic synthesis used
in the reaction can be appropriately set by one skilled in the
art in consideration of, for example, in the case of a Mit-
sunobu reaction, the solubility of the reagent for organic
synthesis with respect to the used solvent, the stoichiometry

of the Mitsunobu reaction, and the like, and in the case of
adding the reagent for organic synthesis as a substitute sub-
stance of triphenylphosphine, it is preferable to add from 1
to 5 equivalents with respect to one equivalent of the dehy-
drated hydroxyl group, and in the case of adding as a substi-
tute substance for diethyl azodicarboxylate, it is preferable
to add from 1 to 5 equivalents with respect to one equivalent
of the dehydrated hydroxyl group.
Use of the Reagent for Organic Synthesis as a Nucleophilic
Scavenger and an Electrophilic Scavenger
By using the reagent for organic synthesis of the present
embodiment as a nucleophilic scavenger and an electrophilic
scavenger, it is possible to capture electrophilic reagents or
nucleophilic reagents added in excess and remaining unreacted
in the reaction liquid, and compounds having electrophilicity
and nucleophilicity produced as byproducts in the chemical re-
action. Alternatively, in the case of using the reagent for
organic synthesis of the present embodiment as a nucleophilic
scavenger, and an electrophilic scavenger, it is also possible
to bond it to the unreacted reaction substrate, and make the
reaction proceed on the reagent for organic synthesis. The
reagent for organic synthesis which can be used in such reac-
tions is not particularly limited, and for example, in the
reagent for organic synthesis shown in Chemical Formula (1), a
reagent for organic synthesis wherein the reagent active site
X is shown by (A) to (C) or (A') to (C) if a nucleophilic
scavenger, or the reagent active site X is shown by (D) to (H)

and (M), or (D') to (H') and (M') if an electrophilic scav-
enger, can be mentioned.
The added amount of the reagent for organic synthesis used
in the reaction can be appropriately set by one skilled in the
art in consideration of the solubility of the reagent for or-
ganic synthesis with respect to the used solvent, and the
electrophilicity and nucleophilicity of the compound to be
captured and the like, and it is preferable to add from 1 to 5
equivalents of the reagent for organic synthesis with respect
to one equivalent of the expected residual amount of the nu-
cleophilic or electrophilic reaction substrate.
For the case of using the reagent for organic synthesis of
the present embodiment as a nucleophilic scavenger, for exam-
ple, a form of use such as the following can be mentioned.
Namely, in the case of carrying out a peptide synthesis
reaction using an active amino acid in an N,N-dimethylfor-
mamide/propionitrile mixed solvent, a peptide bond is formed
when adding an excess amount of the activated amino acid with
respect to the N terminal amino group of the peptide. Because
the excess active amino acid remaining in the reaction system
has electrophilicity, it is easy to form an ester bond with
this by adding the compound shown in Chemical Formula (2).
After the reaction, by adding a solvent such as cyclohexane or
the like, it is possible to recover the nucleophilic scavenger
bonded to the active amino acid from the amide layer, and a
peptide to which 1 amino acid residue is attached, at the N
terminal of the peptide before the reaction, remains in the

reaction system.
Use of the Reagent for Organic Synthesis as a Peptide Synthe-
sis Reagent
Among the reagents for organic synthesis of the present
embodiment, those shown by Chemical Formula (1) where X indi-
cates (M) or (M') can be used as electrophilic scavengers, and
especially, can be used as peptide synthesis reagents. In the
case of use as a peptide synthesis reagent, in the reagent ac-
tive site shown by Chemical Formulas (M) and (M1), a carbon
atom bonded to the hydroxyl group in the reagent active site,
as well as a carbon atom bonded to the hailogen atom which is
not directly bonded to the benzene ring, have electrophilici-
ty, and thus can bond with the carboxyl group of the amino
acid, and thus the peptide synthesis reaction can be carried
out by sequentially forming bonds to an activated amino acid
in the state wherein the carboxyl group is bonded to the
reagent for organic synthesis.
At the completion of the peptide synthesis reaction, by
adding acid to the reagent for organic synthesis separated
from the reaction system, it is possible to easily separate
only the peptide. Here, the reagent for organic synthesis
having a reagent active site (M) or (M') does not activate the
carbonyl group when the amino acid is bonded to the reagent
for organic synthesis, and thus there is no generation of in-
termediates having an oxazolone skeleton which would lead to
racimization of the a carbon, and thus in the process of pep-
tide synthesis, racimization of the peptide does not occur.

Further, applications of the reagent for organic synthesis
having a reagent active site (M) or (M') are not limited to
applications as a reagent for peptide synthesis. Specifical-
ly, for example, applications as a hydrophobic carrier group,
by reacting the reagent for organic synthesis having a reagent
active site with the desired compound, can be mentioned. Such
reagents for organic synthesis used as a hydrophobic carrier
group are also included within the scope of the present inven-
tion.
Use of the Reagent for Organic Synthesis as a Metal Ligand
By using the reagent for organic synthesis as a metal lig-
and, the reagent for organic synthesis can coordinate with and
capture metal ions added to the reaction system as catalysts
or the like.. The reagent for organic synthesis which can be
used for such a reaction is not particularly limited, and for
example, in the reagent for organic synthesis shown by Chemi-
cal Formula (1), a reagent for organic synthesis where X is a
reagent active site shown by (K) or (K') can be mentioned.
The added amount of the reagent for organic synthesis used
in the reaction can be appropriately set by one skilled in the
art in consideration of the solubility of the reagent for or-
ganic synthesis with respect to the solvent, and the normal
coordination number of the metal ion and the like, and it is
preferable to add from 1 to 5 equivalents of the reagent for
organic synthesis with respect to one equivalent of the added
metal ion.
For the case of using the reagent for organic synthesis as

a nucleophilic scavenger, electrophilic scavenger, or metal
ion ligand, in the chemical reaction preceding the reaction
for trapping the excess compounds and the like, it is possible
to use a solvent commonly used in this reaction, and in the
present embodiment, from the point of the solubility of the
reagent for organic synthesis having a hydrophobic carrier
group, it is preferable to use tetrahydrofuran,
dichloromethane, a cyclohexane/N,N-dimethylformamide mixed
solvent or the like as the solvent.
Separation Step
The reagent for organic synthesis of the present embodi-
ment reacts sharply to changes in the solution composition
and/or temperature, and crystallizes. Because of this, it is
possible to crystallize the reagent for organic synthesis us-
ing the means of changing the composition and/or temperature
of the solution. Further, the separation step of the reagent
for organic synthesis can by carried out by liquid liquid ex-
traction separation, by adding a separation solvent which is
immiscible with the reaction solvent used in the reaction
step, but which can easily dissolve the reagent for organic
synthesis.
Separation by Changing the Solution Composition
As a preferred means for changing the solution composi-
tion, for example, the means of adding a poor solvent for the
reagent for organic synthesis to the reaction solution can be
mentioned. Here, by adding a solvent with high affinity for
the reaction solvent, there is no phase separation of the liq-

uid phase, and thus is it possible to easily change the solu-
tion composition. As the poor solvent, it is possible to use
any solvent, and it is possible to use the same solvent used
as the reaction solvent, and a solvent which differs form the
reaction solvent. For example, in the case of using
dichloromethane, tetrahydrofuran and diethylether or the like
as the reaction solvent, it is possible to use acetonitrile,
N,N-dimethylformamide, and methanol and the like as the poor
solvent. By adding the poor solvent to the reaction solvent,
the polarity of the solution increases, and the reagent for
organic synthesis, and the reacted reagent for organic synthe-
sis can crystallize and solid liquid separation becomes possi-
ble. When carrying out the solid liquid separation, it is
possible to use a suction filter such as, for example, a sepa-
ratory funnel, and in order to complete the separation of the
products from a reagent having a hydrophobic carrier group, an
octadecylsilylated (ODS) silica gel filter or an ODS short
column may be used.
Separation by Concentration of the Solution
As another preferable means for changing the solution com-
position, for example, the means of concentrating the solvent
of the solution in which the reagent for organic synthesis,
and the reacted reagent for organic synthesis are dissolved,
can be mentioned. Here, concentrating refers to distilling
away a part of the solvent. When distilling a part of the
solvent, it is preferable to carry out the distillation within
a range wherein the reagent for organic synthesis, and the re-

acted reagent for organic synthesis crystallize, while the
synthesized desired compound does not crystallize. These con-
ditions can be appropriately set by one skilled in the art in
consideration of the added amount of the reagent for organic
synthesis, the estimated produced amount of the desired com-
pound, the solubility of each compound and the like.
Separation by Changing the Solution Temperature
In the separation step, by changing the solution tempera-
ture, it is possible to crystallize and separate the reagent
for organic synthesis and the reacted reagent for organic syn-
thesis. In the present embodiment, as a preferably used means
for changing the solution temperature, there is no particular
limitation so long as it is a means for changing the tempera-
ture of the solution in which the reagent for organic synthe-
sis and the reacted reagent for organic synthesis are dis-
solved. Specifically, the means of cooling the solution can
be mentioned. For example, in the case of using cyclohexane
as the reaction solvent, by cooling to 5°C or less, it is pos-
sible to crystallize the reagent for organic synthesis and the
reacted reagent for organic synthesis. Further, in the case
of using N,N-dimethylformamide as the reaction solvent, by
heating in the reaction step, the solubility of the reagent
for organic synthesis increases, and by cooling after the re-
action, the reagent for organic synthesis and the reacted
reagent for organic synthesis can be crystallized.
In the case of crystallizing the reagent for organic syn-
thesis by changing the solution composition and the solution

temperature, by adding octadecylsilylated silica gel, glass
beads or the like as crystallization seeds, it is possible to
easily form the crystals.
Separation by Liquid Liquid Extraction
In the separation step, by adding a separation solvent
which does not mix with the reaction solvent in which the
reagent for organic synthesis is dissolved in the reaction
step, and for which the solubility of the reagent for organic
synthesis is greater than the solubility of the reagent for
organic synthesis in the reaction solvent, it is possible to
dissolve the reagent for organic synthesis and the reacted
reagent for organic synthesis in the separation solvent. By
separating with a separatory funnel the separation solvent in
which the reagent for organic synthesis, and the reacted
reagent for organic synthesis are dissolved, it is possible to
easily separate the reagent for organic synthesis, and the re-
acted reagent for organic synthesis from the reaction solvent.
In the present embodiment, the separation solvent which
can be used is not particularly limited, and in the case of
using acetonitrile, propionitrile, and N,N-dimethylformamide
or the like as a reaction solvent, for example, cyclohexane,
and decalin or the like can be used.
Namely, for example, in the case of using N,N-dimethylfor-
mamide as the reaction solvent, by adding cyclohexane as the
separation solvent to the reaction system after the completion
of the chemical reaction, heating, and then cooling, the
reagent for organic synthesis, and the reacted reagent for or-

ganic synthesis are selectively distributed into the cyclohex-
ane phase. By separating the cyclohexane phase with a separa-
tory funnel, it is possible to obtain an N,N-dimethylformamide
solution from which the reagent for organic synthesis, and the
reacted reagent for organic synthesis have been removed.
In the method of organic synthesis reaction of the present
embodiment, after separating the reagent for organic synthe-
sis, it is possible to further carry out a process for sepa-
rating the reagent for organic synthesis and an atomic group
bonded to the reaction active site, and to isolate the sepa-
rated atomic group. In such a case, as a reagent which can be
used when separating the reagent for organic synthesis and the
atomic group bonded to the reaction active site, trifluoroac-
etate,.and acids such as hydrochloric acid and the like; bases
such as sodium hydroxide; as well as hydrogenation catalysts
such as palladium and the like can be mentioned. Among these,
trifluoroacetate can be preferably used.
EXAMPLES
The present invention is explained below with reference to
the following Examples, but the present invention is not in
any way limited by these examples.
Example 1: Synthesis of an Amine Having a Hydrophobic Carrier
Group
One gram of 2,4-dihydroxybenzaldehyde, 8.4 g of 1-bromod-
ocosane, and 6 g of potassium carbonate were dissolved in 20
ml of N,N-dimethylformamide, and reacted for 8 hours under a

nitrogen gas flow at 80°C. After confirming the completion of
the reaction by thin layer chromatography, 20 ml of toluene
and 10 ml of water were added to the reaction liquid and
stirred for 5 min at 80°C. The toluene layer was separated
with a separatory funnel and after removal by distillation of
the solvent, 50 ml of methanol were added and crystals were
precipitated. This solution was subjected to suction filtra-
tion with a separatory funnel and 6.97 g of crude crystals
were obtained. After dissolving the crude crystals in 200 ml
of hexane at 70°C and recrystallizing at room temperature,
suction filtration was again carried out with a separatory
funnel, and 4.7 g of the desired compound 3 were obtained.
The yield was 85%. Compound 3;2,4-bis(docosyloxy)benzalde-
hyde.
Then, 1.9 g of compound 3 were set aside and dissolved in
dichloromethane, and 500 mg of hydroxyamine hydrochloride, and
an excess amount of triethylamine were added and reacted for 6
hours at room temperature. After the completion of the reac-
tion, the solution was concentrated, and 50 ml of acetonitrile
were added and the product was crystallized. This solution
was suction filtered with a separatory funnel and 1.9 g of
compound 4 were obtained. The yield was 98%. Compound 4;2,4-
bis(docosyloxy)benzaldehyde oxime.
Next, 770 mg of compound 4 were set aside and dissolved in
tetrahydrofuran, 150 mg of lithium aluminum hydride were added
at room temperature and stirred, and after this, heating and
refluxing were carried out. After the completion of the reac-

tion was confirmed by thin layer chromatography, 5 ml of
methanol and 50 ml of toluene were added and the organic layer
was washed with an aqueous solution of 1 N hydrochloric acid,
neutralized with a saturated sodium hydrogen carbonate solu-
tion, and washed with a saturated saline solution. The organ-
ic layer was separated and vacuum distillation removed, and
after this, 50 ml of methanol were added and crystals precipi-
tated. This solution was suction filtered with a separatory
funnel and 719 mg of compound 5 were obtained. The yield was
95%. Compound 5;(2,4-bis(docosyloxy)phenyl)methane amine.
The above reactions are shown below.

Structural Analysis of Compound 3
1H-NMR (CDCl3, 300 MHz) δ 10.32 (1H, s) , 7.78 (1H, d,
j=8.62 HZ), 6.50 (1H, dd j=8.62, 2.20 Hz), 6.41 (1H, d, J=
2.20 Hz), 4.04 (1H, d, j=6.60 Hz), 3.99 (1H, d, j=6.60 Hz),
1.81 (4H, m),1.51-1.18 (76H, m), 0.88 (6H, t, j= 6.60 Hz)
Structural Analysis of Compound 4
1H-NMR (CDCl3, 300 MHz) δ 8.45 (1H, s), 7.65 (1H, d, j=8.40
Hz), 6.46 (1H, dd j=8.40, 2.20 Hz), 3.96 (2H, t, j= 6.42 Hz),
3.95 (2H, t, j=6.42 HZ), 1.78 (4H, m), 1.50-1.15 (76H, m),
0.88 (6H, t, j=6.80 HZ)
Structural Analysis of Compound 5

1H-NMR (CDCl3, 300 MHz) 5 8.45 (1H, s), 7.65 (1H, d, j=8.40
Hz), 6.46 (1H, dd j=8.40, 2.20 Hz), 3.96 (2H, t, j= 6.42 Hz),
3.95 (2H, t, j=6.42 HZ), 1.78 (4H, m), 1,50-1.15 (76H, m),
0.88 (6H, t, J= 6.80 Hz)
Example 2: Synthesis of an Isocyanate Having a Hydrophobic
Carrier Group
An amount of 371 mg (0.4 mmol) of 3,4,5-tris(octadecyloxy)
benzoic acid was dissolved in 5 ml of toluene, and mixed with
412 mg (1.50 mmol) of diphenylphosphoryl azide (DPPA) and 30
mg (0.4 mmol) of triethylamine. This was stirred for 3 hours
at room temperature, and then, heated to 90°C, and further re-
acted for 3.5 hours. After the completion of the reaction,
acetonitrile was added, and after the precipitation of crys-
tals, suction filtration was carried out with a separatory
funnel and 333 mg of compound 6 were obtained. The yield was
90%. Compound 6;5-isocyanate-1,2,3-tris(octadecyloxy)benzene.
The above reactions are shown below.

Structural Analysis of Compound 6
1H-NMR (CDCl3, 400 MHz) δ 6.20 (2H, s), 3.98-3.92 (6H, m),
1.82-1.69 (6H, m), 1.49-1.23 (84H, m), 0.88 (9H, t, j=6.60 Hz)
Example 3: Synthesis of a Chloroformate Having a Hydrophobic
carrier group
An amount of 4.43 g of methyl 3,5-bis(docosyloxy)benzoate

was dissolved in 100 ml of tetrahydrofuran, and 240 mg of
lithium aluminum hydride were introduced and stirred at room
temperature. After the completion of the reaction was con-
firmed by thin layer chromatography, 1 ml of methanol was
added and the reaction was stopped. After this, 30 ml of 1 N
hydrochloric acid was added, and the extracted organic layer
was washed two times with 30 ml of 1 N hydrochloric acid, once
with 30 ml of a saturated aqueous solution of sodium hydrogen
carbonate, and twice with 30 ml of saturated saline solution,
and dried with magnesium sulfate. After vacuum distillation
of the solution, 100 ml of methanol were added and crystals
precipitated, and suction filtration was carried out using a
separatory funnel to obtain 3.62 g of compound 7. The yield
was 80%. Compound 7;3,5-bis(docosyloxy)benzyl alcohol
An amount of 5 g of compound 7 was dissolved in 50 ml of
toluene, 4.86 g of triphosgene were added, and reacted for 2
hours under a nitrogen gas flow at room temperature. After
this, the reaction liquid was heated to 40°C, and further
stirred for 1 hour. After the completion of the reaction was
confirmed by thin layer chromatography, drying was carried out
for 2 hours at 3 mmHg under a vacuum pump at 4 0°C to obtain
5.1 g of compound 8. The yield was 94%. Compound 8;3,5-bis
(docosyloxy)benzylcarbonochloridate
The above reactions are shown below.


Structural Analysis of Compound 7
1H-NMR (CDCl3, 300 MHz) δ 6.49 (2H, d, j=2.20 Hz), 6.37
(1H, t, j=2.20 HZ), 4.60 (2H, s), 3.92 (4H, t, j= 6.60 Hz),
1.76 (4H, m), 1.49-1.18 (76H, m), 0.88 (6H, t, j=6.60 Hz)
Structural Analysis of Compound 8
1H-NMR (CDCl3, 300 MHz) δ 6.49 (2H, d, j=2.20 Hz), 6.45
(1H, t, j=2.20 HZ), 5.20 (2H, s), 3.93 (4H, t, j= 6.79 Hz),
1.76 (4H, m), 1.52-1.13 (76H, m), 0.88 (6H, t, j=6.60 Hz)
Example 4: Synthesis of a Carbamate Having a Hydrophobic car-
rier group
An amount of 756 mg (1.0 mmol) of the compound 7 synthe-
sized in Example 3 was set aside, and dissolved in 20 ml of
dichloromethane. Then, 810 mg (5.0 mmol) of 1,1'-carbonyldi-
imidazole was added, and stirred for 4 hours at room tempera-
ture. After the completion of the reaction was confirmed by
thin layer chromatography, the solvent was distilled under a
vacuum, acetonitrile was added, and crystallization occurred.
This was suction filtered using a separatory funnel, and 850
mg of compound 9 were obtained. The yield was 99%. Compound
9; 3,5-bis(docosyloxy)benzyl 1H-imidazole-1-carboxylate
The above reactions are shown below.


Structural Analysis of Compound 9
1H-NMR (CDCl3, 400 MHz) δ 8.15 (1H, m), 7.44 (1H, m), 7.06
(1H, m), 6.53 (2H, d, j= 2.21 Hz), 6.46 (1H, t, j=2.21 Hz),
5.32 (2H, s), 3.93 (4H, t, j=6.42 Hz), 1.75 (4H, m), 1.49-1.16
(76H, m), 0.88 (6H, t, j=6.97 Hz)
Example 5: Synthesis of a Bromine Compound Having a Hydropho-
bic Carrier Group
To a dried recovery flask, 915.0 mg (1 mmol) of 3,4,5-
trisoctadecyloxybenzyl alcohol were added, and dissolved in 10
ml of dichloromethane. Then, 406.3 mg (1.5 mmol) of phospho-
rus tribromide were added, and stirred for 3 hours at room
temperature. After confirming the completion of the reaction
by thin layer chromatography, 1 ml of water was added and the
reagent was deactivated. After this, liquid liquid extraction
was carried out with hexane, and then washing was carried out
with a saturated saline solution, and an organic phase was ob-
tained. The solvent was distilled under a vacuum from this
organic phase, and suction filtration was carried out using a
separatory funnel, and 988.1 g of compound 10 were obtained.
The yield was 99%. Compound 10;3,4,5-trisoctadecyloxybenzyl-
bromide


Structural Analysis of Compound 10
1H-NMR (CDCl3, 400 MHz) δ 6.57 (2H, s), 4.43 (2H, s), 3.98-
3.92 (6H, m), 1.82-1.69 (6H, m), 1.50-1.42 (6H, m), 1.33-1.23
(84H, m), 0.88 (9H, t, j=7.0 Hz)
Infrared Absorption Spectrum (KBr)62954, 2920, 2848, 1591,
1504, 1466, 1441, 1394, 1246, 1213, 1115 (units: cm-1)
Example 6: Synthesis of a Basic Compound Having a Hydrophobic
Carrier Group-
Into a dried recovery flask 1.4 6 g (1.5 mmol) of compound
10 synthesized in Example 5 were set aside and dissolved in 20
ml of N, N-dimethylf ormamide. Then, 443.1 rng (2 equivalents)
of potassium carbonate, 369.4 mg (1 equivalent) of tetrabuty-
lammonium iodide, and 1.05 g (5 equivalents) of 1,5,7-triaz-
abicyclo[4,4,0] deca-5-ene were added, and stirred for 4 hours
at 80°C. After the completion of the reaction was confirmed
by thin layer chromatography, liquid liquid extractions were
carried out with hexane, and then with a. saturated saline so-
lution, and an organic phase was obtained. This organic phase
was distilled under a vacuum, methanol was added and crystal-
lization occurred, and then suction filtration was carried out
with a separatory funnel, and 1.3 g of compound 11 were ob-

tained. The yield was 84%. Compound 11; 1-(3,4,5-tris(oc-
tadecyloxy) benzyl) -2, 3, 4,6,7, 8-hexahydro-1H-pyrimidot 1, 2-a]
pyrimidine.
The above reactions are shown below.

Structural Analysis of Compound 11
1H-NMR (CDCl3, 600 MHz) δ 6.46 (2H, s), 4.49 (2H, s), 3.94
(4H, t, j=6.6), 3.91 (2H, t, j= 6.6), 3.41 (2H, t, j=5.5),
3.18 (2H, t, j=5.9), 3.13 (2H, t, j=5.9), 3.03 (2H, t, j=5.9),
1.89 (4H, m), 1.79-1.70 (6H, m), 1.48-1.43 (6H, m), 1.35-1.21
(84H, m), 0.87 (9H, t, j=7)
Infrared Absorption Spectrum (KBr): 2954, 2916, 2850,
1593, 1504, 1468, 1435, 1381, 1228, 1115, 835 (units: cm-1)
Example 7: Synthesis of a Triphenylphosphine Having a Hy-
drophobic Carrier Group
An amount of 7 56 mg (1.0 mmol) of the compound 7 synthe-
sized in Example 3 was set aside and dissolved in 20 ml of
dichloromethane. Then, 612 mg (2.0 mmol) of 4-(diphenylphos-
phino) benzoic acid, 25 mg (0.2 mmol) of dimethylaminopyri-
dine, 631 mg (5.0 mol) of dicyclohexylcarbodiimide were added,
and stirred for 4 hours at room temperature. After the com-
pletion of the reaction was confirmed by thin layer chromatog-

raphy, the solvent was distilled under a vacuum, and acetoni-
trile was added and crystallization occurred, and suction fil-
tration was carried out using a separatory funnel, and 1.0 g
of compound 12 were obtained. The yield was 96%. Compound
12;3,5-bis(docosyloxy)benzyl-4-(diphenylphosphino)benzoic acid
The above reactions are shown below.

Structural Analysis of Compound 12
1H-NMR (CDCl3, 400 MHz) 5 8.00 (2H, dd, j=1.28 Hz), 7.39-
7.27 (12H, m), 6.53 (2H, d, j=2.01 Hz), 6.41 (1H, t, j= 2.01
Hz), 5.26 (2H, s), 3.92 (4.H, m), 1.75 (4H, m), 1.49-1.14 (76H,
m), 0.88 (6H, t, j=6.97 Hz)
Example 8: Synthesis of an Azodicarboxylate Ester Having a Hy-
drophobic Carrier Group
An amount of 8 50 mg (1.0 mmol) of the compound 9 synthe-
sized in Example 4 was set aside, and dissolved in 10 ml of
toluene. Then, 312 mg (3.0 mmol) of ethyl carbazate, and 303
mg (3.0 mmol) of triethylamine were added, and stirred for 18
hours at 120°C. After completion of the reaction, the solvent
was distilled, and 100 ml of acetonitrile were added, and the
precipitated crystals were suction filtered, and 798 mg of
compound 13 were obtained. The yield was 90%. Next, 888 mg
of compound 13 (1.0 mmol) were set aside and after dissolving
in 10 ml of dichloromethane, 644 mg (2.0 mmol) of iodobenzene

acetate were added, and stirred for 3 hours at room tempera-
ture. After confirming the completion of the reaction by thin
layer chromatography, the solvent was distilled under a vacu-
um, and 10 ml of acetonitrile were added and crystallization
occurred. Suction filtration was carried out using a separa-
tory funnel and the crystals were separated, and 620 mg of
compound 14 were obtained. The yield was 7 0%. Compound 13;1-
(3,5-bis(docosyloxy)benzyl)-2-ethylhydrazine-l,2-dicarboxy-
late. Compound 14;1-(3,5-bis(docosyloxy)benzyl)-2-ethyl-
diazine-1,2-dicarboxylate.
The above reactions are shown below.

Structural Analysis of Compound 13
1H-NMR (CDCl3, 400 MHz) δ 6.45 (2H, d, j=2.20 Hz), 6.37
(1H, t, j=2.20 HZ), 5.07 (2H, s), 4.19 (2H, q, j= 7.34 Hz),
3.89 (4H, t, j=6.60 HZ), 1.73 (4H, m), 1.46-1.14 (76H, m),
0.86 (6H, t, j=6.60 HZ)
Structural Analysis of Compound 14
1H-NMR (CDCl3, 400 MHz) δ 6.52 (2H, d, j=2.20 Hz), 6.39
(1H, t, j=2.20 HZ), 5.32 (2H, s), 4.49 (2H, m), 3.89 (4H, m),
1.73 (4H, m), 1.46-1.14 (76H, m), 0.86 (6H, t, j=6.60 Hz)
Example 9: Scavenging of 4-Chlorobenzylamine Using an Iso-
cyanate Having a Hydrophobic carrier group
Amounts of 141 mg (1.0 mmol) of 4-chlorobenzylamine and

183 mg (1.0 mmol) of N-(4-chlorobenzyl)acetamide were dis-
solved in 20 ml of dichloromethane. To the solution, 1.0 g
(1.1 mmol) of the compound 6 synthesized in Example 2 were
added, and after stirring for 10 minutes, 50 ml of acetoni-
trile were added. After distilling the dichloromethane under
a vacuum at room temperature, the crystals were filtered with
a separatory funnel. On distilling the filtrate, N-(4-
chlorobenzyl) acetamide was quantitatively recovered, and the
crystals were compound 15. Compound 15;1-(4-chlorobenzyl)-3-
(3,4,5-tris(octadecyloxy)phenyl)urea
The above reactions are shown below.

Structural Analysis of Compound 15
1H-NMR (CDCl3, 300 MHz) δ 7.10 (4H, m.), 6.45 (2H, s), 6.39
(2H, m), 3.90 (6H, m), 1.77 (6H, m), 1.53-1.17 (90H, m), 0.86
(6H, t, j=6.60 HZ)
Example 10: Synthesis Reaction of Diketopiperazine Using a
Base Having a Hydrophobic Carrier Group
An amount of 278 mg (0.2 mmol) of 3,4,5-tris(octadecyloxy)
benzyl-1-(2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-
phenylpropanoyl)pyrrolidine-2-carboxylate were dissolved in 20
ml of dichloromethane. To this, 205 mg (0.2 mmol) of the com-

pound 11 synthesized in Example 6 were added, and stirred for
7 hours. After the reaction, 50 ml of acetonitrile were
added. After distilling the dichloromethane under a vacuum at
room temperature, the crystals were filtered with a separatory
funnel. The filtrate was vacuum distilled, and 35.1 mg of
diketopiperazine were obtained. The yield was 72%.
Comparative Example 1: Synthesis Reaction of Diketopiperazine
Using a Base Carried on a Polystyrene
An amount of 278 mg (0.2 mmol) of 3, 4, 5-tris(octadecyloxy)
benzyl-1-(2-(((9H-fluorene-9-yl)methoxy)carbonylamino)-3-
phenylpropanoyl)pyrrolidine-2-carboxylate were dissolved in 20
ml of dichloromethane. To this, 600 mg (amino group equiva-
lent 1.2 mmol) of "TBD-methyl polystyrene" (manufactured by
Novabiochem) was added and stirred for 21 hours. The reaction
liquid was filtered, and after distilling the solvent, 50 ml
of acetonitrile were added. After filtering the crystals in a
separatory funnel, the filtrate was vacuum distilled, and 18.5
mg of diketopiperazine were obtained. The yield was 38%.
Comparative Example 2: Synthesis Reaction of Diketopiperazine
Using a Base Carried on a Silica Gel
An amount of 278 mg (0.2 mmol) of 3,4,5-tris(octadecyloxy)
benzyl-1-(2-(((9H-fluorene-9-yl)methoxy)carbonylamino)-3-
phenylpropanoyl)pyrrolidine-2-carboxylate was dissolved in 20
ml of dichloromethane. To this, 1200 mg (amino group equiva-
lent 1.2 mmol) of "Si-TBD" (manufactured by Sigma Aldrich) was
added and stirred for 21 hours. The reaction liquid was fil-
tered, and after the distillation of the solvent, 50 ml of

acetonitrile were added. After filtration of the crystals
with a separatory funnel, the filtrate was vacuum distilled,
and 7.3 mg of diketopiperazine were obtained. The yield was
15%.
The reactions of Example 10, and Comparative Examples 1
and 2 are shown below.

Example 11: Mitsunobu Reaction Using an Azodicarboxylate Ester
Having a Hydrophobic Carrier Group
Into an recovery flask, 16 mg (0.1 mmol) of 2-(4-
methoxyphenyl)acetic acid, and 7 mg (0.1 mmol) of isopropanol
were added, and dissolved in 5 ml of tetrahydrofuran. To
this, 52 mg (0.2 mmol) of triphenylphosphine, and 177 mg (0.2

mmol) of the compound 14 of Example 8 were added, and stirred
for 24 hours at room temperature. The solvent was distilled
under a vacuum, acetonitrile was added, and filtration was
carried out with an octadecylsilyl silicei packed syringe, and
from the filtrate, 16.7 mg of isopropyl-2-(4-methoxyphenyl)ac-
etate was obtained. The yield was 70%.
The above reactions are shown below.

Example 12: Peptide Synthesis Reaction
An amount of 785 mg (1.0 mmol) of methyl 3,5-bis(docosy-
loxy)benzoate was dissolved in 20 ml of tetrahydrofuran, and
18 ml (9 equivalents) of 4-chlorophenylmagnesiumbromide
tetrahydrofuran solution was added, and stirring was carried
out for 2 hours at 76°C. After confirming the completion of
the reaction by thin layer chromatography, 30 ml of 1 N hy-
drochloric acid was added and the reaction was stopped. After
this, extraction was carried out 3 times with 30 ml of hexane,
and the obtained organic phase was further washed one time
with 30 ml of 1 N hydrochloric acid, one time with saturated
sodium hydrogen carbonate, and one time with saturated saline
solution, and dried with magnesium sulfate. After vacuum dis-
tillation of the solvent, 100 ml of methemol was added and
crystals were precipitated, and suction filtration was carried

out with a separatory funnel to obtain 780 mg of compound 16.
The yield was 80%. Compound 16;3,5-bis(docosyloxy)phenyl-4,4-
dichlorophenyl alcohol.

Structural Analysis of Compound 16
1H-NMR (CDCl3, 400 MHz) δ 7.30-7.26 (4H, m), 7.23-7.17
(4H, m), 6.44-6.32 (2H, m), 6.32-6.30 (1H, m), 3.84 (4H, t,
j=6.6 HZ), 1.67-1.63 (4H, m), 1.27-1.24 (76H, m), 0.88 (6H, t,
j=7.0 HZ)
An amount of 294 mg (0.3 mmol) of compound 16 were dis-
solved in 5 ml of dichloromethane, and 1 ml of acetyl chloride
was added and reacted for 1 hour at 45°C. After confirming
the completion of the reaction by thin layer chromatography,
vacuum distillation was carried out and the solvent was dis-
tilled, and a crystalline substance (compound 17) was ob-
tained. The thus obtained crystals were dissolved in 10 ml of
dichloromethane, and 180 mg (1.5 equivalents) of Fmoc-Cys
(tBu)-OH, and 262 μl (5 equivalents) of diisopropylethylamine
were added and reacted for 30 min at 0°C. After confirming
the completion of the reaction by thin layer chromatography,
500 μl of diazabicycloundecene were added, and further reacted
for 10 minutes. After again confirming the completion of the
reaction by thin layer chromatography, 100 ml of acetonitrile

was added, and the solution was gradually vacuum filtered and
crystals were precipitated, and suction filtration was carried
out using a separatory funnel and a crystalline substance was
obtained.
The thus obtained crystalline substance was dissolved in
10 ml of dichloromethane, and 175 mg (1.5 equivalents) of
Fmoc-Phe-OH, 188 μl (4 equivalents) of diisopropylcarbodi-
imide, and 162 mg (4 equivalents) of 1-hydroxybenzotriazole
were added and reacted for 1 hr at room temperature. After
confirming the completion of the reaction by thin layer chro-
matography, 100 ml of acetonitrile were added, and the solvent
was gradually vacuum distilled and crystals were precipitated,
and suction filtration was carried out using a separatory fun-
nel and 371 mg of compound 18 were obtained. The yield was
83%. The thus obtained crystalline substance was dissolved in
10 ml of a previously adjusted 0.1% trifluoroacetic
acid/dichloromethane solution and reacted for 1 hour. After
confirming the completion of the reaction by thin layer chro-
matography, 100 ml of acetonitrile were added, and the solu-
tion was gradually vacuum distilled and crystals were precipi-
tated, and suction filtration was carried out using a separa-
tory funnel. By vacuum distillation of the obtained solution,
the desired compound Fmoc-Phe-Cys(tBu)-OH (compound 19) was
obtained. Further, confirmation of the desired product was
carried out in a mass spectrograph. Compound 17; chloro-3, 5-
bis(docosyloxy)phenyl-4,4-dichlorophnylmethane


Structural Analysis of Compound 17
1H-NMR (CDCl3, 300 MHz) μ 7.36-7.06 (8H, m), 6.45-6.20
(3H, m), 4.01-3.59 (4H, m), 1.83-1.49 (4H, m), 1.40-1.10 (76H,
m), 0.88 (6H, t, j=6.6 Hz)
Structural Analysis of Compound 19
HRMS m/z (ESI) calculated for [ M+H] + 547.2267; found
547.2274
Example 13: Synthesis of Reagent for Organic Synthesis having
a Trityl Group
An amount.of 1570 mg (2.0 mmol) of 3,5 bis(docosyloxy)
methyl benzoic acid was dissolved in 30 ml of tetrahydrofuran,
and 9 ml of a solution of phenylmagnesiumbromide tetrahydrofu-
ran was added and stirring was carried out for 2 hours at 76°C
After confirming the completion of the reaction by thin
layer chromatography, 40 ml of 1 N hydrochloric acid was added
and the reaction was stopped. After this, extraction was car-
ried out 3 times with 30 ml of hexane, and the extracted or-
ganic phase was washed once with 30 ml of 1 N hydrochloric
acid, once with a saturated aqueous solution of sodium hydro-
gen carbonate, and once with a saturated saline solution, and
dried with magnesium sulfate. After part of the solution was
vacuum distilled, 100 ml of methanol were added to the solu-
tion and crystals precipitated, and suction filtration was

carried out with a separatory funnel, and 1456 mg of compound
20 were obtained. The yield was 80%. Compound 20;3,5-bis(do-
cosyloxy)phenyl-diphenyl alcohol

Structural Analysis of Compound 20
1H-NMR (CDCl3, 300 MHz) δ 7.70-6.80 (10H, m), 6.45-3.38
(2H, m), 6.38-6.34 (1H, m), 3.84 (4H, t, j=6.6 Hz), 1.74-1.56
(4H, m), 1.50-1.10 (76H, m), 0.88 (6H, t, j=6.6 Hz)
An amount of 1000 mg (1.1 mmol) of compound 20 was dis-
solved in 30 ml of dichloromethane, and 234 μl (3.3 mmol) of
thionyl chloride was added and reacted for 1 hour at room tem-
perature. After confirming the completion of the reaction by
thin layer chromatography, the solvent was vacuum distilled,
and a crystalline substance (compound 21) was obtained quanti-
tatively. Compound 21;chloro-3,5-bis(docosyloxy)phenyl-
diphenylmethane

1H-NMR (CDCl3, 300 MHz) δ 7.33-7.22 (lOH, m), 6.40-6.30
(3H, m), 3.83 (4H, t, j=6.6 Hz), 1.80-1.60 (4H, m), 1.50-1.10

(76H, m), 0.88 (6H, t, j=6.6 Hz)
Example 14: Reaction of Reagent for Organic Synthesis Having a
Trityl Group and Amino Acid
An amount of 513 mg (3.3 mmol) of H-Ser-OMe was dissolved
in 20 ml of dichloromethane. Then, 1150 μl (6.6 mmol) of di-
isopropylethylamine was added and in addition, the full amount
of compound 21 synthesized in Example 13 was added and stir-
ring was carried out for 30 minutes. After confirming the
completion of the reaction by thin layer chromatography, 100
ml of acetonitrile were added, and the dichloromethane was
vacuum distilled at room temperature. By carrying out suction
filtration on this with a separatory funnel, a crystalline
substance (compound 22) was quantitatively obtained. Compound
22;2-(3,5-bis(docosyloxy)phenyl)-diphenylamino-3-hydrox-
ypropane ethyl ester

Structural Analysis of Compound 22
1H-NMR (CDCl3, 300 MHz) δ 7.60-7.10 (10H, m), 6.64-6.60
(2H, m), 6.29-6.25 (1H, m), 3.82 (4H, t, j=6.6 Hz), 3.78-3.60
(2H, m), 3.60-3.50(1H, m), 3.32 (3H, s), 1.74-1.56 (4H, m),
1.50-1.10 (76H, m), 0.88 (6H, t, j=6.6 Hz)
INDUSTRIAL APPLICABILITY

The reagent for organic synthesis and the method of organic
synthesis reaction of the present invention make it possible
to accelerate the research and development of pharmaceuticals
and the like by compound libraries, and in addition contribute
to technical innovation in the biochemical and chemical
industries. Because the reagent can be efficiently used and
recovered, it provides an innovative technology which
contributes to the development of "green chemistry".

1. [Amended] A reagent for organic synthesis which can be
used for organic synthesis reactions, shown in the following
Chemical Formula (1), and having a property of reversibly
changing from a liquid phase state to a solid phase state
according to changes in at least one selected from the group
consisting of solution composition and solution temperature:
[Chemical Formula 1]

wherein R1 to R5 may be the same or different, and
represent hydrogen, halogen, alkyl group with a carbon number
of 1 to 30 which may have a substituent group, alkoxyl group
with a carbon number of 1 to 30 which may have a substituent
group, aryl group with a carbon number of 1 to 30 which may
have a substituent group, acyl group with a carbon number of i
to 30 which may have a substituent group, thioalkyl group with
a carbon number of 1 to 30 which may have a substituent group,
dialkylamino group with a carbon number of 1 to 30 which may
have a substituent group, nitro group, or amino group; and at
least two of R1 to R5 are groups with a carbon number of 18 to
30, and X represents a reagent active site shown by the






wherein, in the formulas (A) to (F) and (H) to (M), Y is
an ester bond, ether bond, amide bond, thioester bond, sulfide
bond, urea bond, carbamate bond, or carbonate bond, or a
alkylene group with a carbon number of 1 to 10 which may have
one of these bonds, and in formulas (M) and (M'), m and n are
each independently 0 or 1, Za is a chlorine atom or a bromine
atom, Zb is a hydroxyl group, chlorine atom, or a bromine atom.
2. [Deleted]
3. [Amended] A reagent for organic synthesis according to
claim 1, wherein in said Chemical Formula (1), R2 and R4 are a
docosyloxy group (C22H45O-), R1, R3 and R5 are hydrogen.
4. The reagent for organic synthesis according to claim 3,
wherein the reagent active site X in said Chemical Formula (!)
is the functional group shown by said formula (M) or (M').
5. [Amended] A reagent for organic synthesis which can be
used for organic synthesis reactions, shown in the following
Chemical Formula 2, and having a property of reversibly
changing from a liquid phase state to a solid phase state

according to changes in at least one selected from the group
consisting of solution composition and solution temperature.
[Chemical Formula 14]

6. [Amended] A method of organic synthesis reaction using the
reagent for organic synthesis according to any one of claims 1,
3, 4, 5, or 7, comprising a reaction step of carrying out a
reaction wherein said reagent for organic synthesis is
dissolved in a reaction system where the reagent active site X
of Chemical Formula (1) participates in the reaction, and
after this, a separation step of separating the reagent for
organic synthesis and a reacted reagent for organic synthesis.
7. [Added] A reagent for organic synthesis which can be
used for organic synthesis reactions, shown in the following
Chemical Formula (23) or (23'),and having a property of
reversibly changing from a liquid phase state to a solid phase
state according to changes in at least one selected from the
group consisting of solution composition and solution
temperature.
[Chemical Formula 15]

A reagent for organic syntheses with which a chemical reaction can be conducted in a liquid phase and unnecessary compound(s) can be easily separated at low cost from the liquid phase after completion of the reaction. The reagent for organic syntheses reversibly changes from a liquid-phase state to a solid-phase state with changes in solution composition and/or solution
temperature, and is for use in organic synthesis reactions. This reagent for organic syntheses facilitates process developments. With the reagent, researches on and developments of, e.g., medicines through, e.g., compound library syntheses, etc. can be accelerated. It can hence contribute to a technical innovation in the biochemical industry and chemical industry.

Documents:

3984-KOLNP-2008-(11-06-2014)-CLAIMS.pdf

3984-KOLNP-2008-(11-06-2014)-CORRESPONDENCE.pdf

3984-KOLNP-2008-(11-06-2014)-FORM-13.pdf

3984-KOLNP-2008-(11-06-2014)-OTHERS.pdf

3984-KOLNP-2008-(16-12-2013)-CORRESPONDENCE.pdf

3984-KOLNP-2008-(16-12-2013)-FORM-3.pdf

3984-KOLNP-2008-(16-12-2013)-OTHERS.pdf

3984-KOLNP-2008-(16-12-2013)-PETITION UNDER RULE 137.pdf

3984-KOLNP-2008-(30-12-2013)-ABSTRACT.pdf

3984-KOLNP-2008-(30-12-2013)-CLAIMS.pdf

3984-KOLNP-2008-(30-12-2013)-CORRESPONDENCE.pdf

3984-KOLNP-2008-(30-12-2013)-FORM-13.pdf

3984-KOLNP-2008-(30-12-2013)-FORM-2.pdf

3984-KOLNP-2008-(30-12-2013)-OTHERS.pdf

3984-kolnp-2008-abstract.pdf

3984-KOLNP-2008-ASSIGNMENT-1.1.pdf

3984-KOLNP-2008-ASSIGNMENT.pdf

3984-KOLNP-2008-CANCELLED PAGES.pdf

3984-kolnp-2008-claims.pdf

3984-KOLNP-2008-CORRESPONDENCE-1.1.pdf

3984-KOLNP-2008-CORRESPONDENCE-1.2.pdf

3984-kolnp-2008-correspondence.pdf

3984-kolnp-2008-description (complete).pdf

3984-KOLNP-2008-EXAMINATION REPORT.pdf

3984-KOLNP-2008-FORM 1-1.1.pdf

3984-kolnp-2008-form 1.pdf

3984-KOLNP-2008-FORM 13.pdf

3984-KOLNP-2008-FORM 18-1.1.pdf

3984-KOLNP-2008-FORM 18.pdf

3984-KOLNP-2008-FORM 3-1.1.pdf

3984-kolnp-2008-form 3.pdf

3984-KOLNP-2008-FORM 5-1.1.pdf

3984-kolnp-2008-form 5.pdf

3984-KOLNP-2008-FORM 6-1.1.pdf

3984-KOLNP-2008-FORM 6.pdf

3984-KOLNP-2008-GRANTED-ABSTRACT.pdf

3984-KOLNP-2008-GRANTED-CLAIMS.pdf

3984-KOLNP-2008-GRANTED-DESCRIPTION (COMPLETE).pdf

3984-KOLNP-2008-GRANTED-FORM 1.pdf

3984-KOLNP-2008-GRANTED-FORM 2.pdf

3984-KOLNP-2008-GRANTED-FORM 3.pdf

3984-KOLNP-2008-GRANTED-FORM 5.pdf

3984-KOLNP-2008-GRANTED-LETTER PATENT.pdf

3984-KOLNP-2008-GRANTED-SPECIFICATION-COMPLETE.pdf

3984-kolnp-2008-international preliminary examination report.pdf

3984-kolnp-2008-international publication.pdf

3984-KOLNP-2008-INTERNATIONAL SEARCH REPORT & OTHERS.pdf

3984-kolnp-2008-international search report.pdf

3984-KOLNP-2008-OTHERS-1.1.pdf

3984-kolnp-2008-others.pdf

3984-KOLNP-2008-PA-1.1.pdf

3984-KOLNP-2008-PA.pdf

3984-kolnp-2008-pct priority document notification.pdf

3984-kolnp-2008-pct request form.pdf

3984-KOLNP-2008-PETITION UNDER RULE 137.pdf

3984-KOLNP-2008-REPLY TO EXAMINATION REPORT-1.1.pdf

3984-KOLNP-2008-REPLY TO EXAMINATION REPORT.pdf

3984-kolnp-2008-specification.pdf


Patent Number 263291
Indian Patent Application Number 3984/KOLNP/2008
PG Journal Number 43/2014
Publication Date 24-Oct-2014
Grant Date 17-Oct-2014
Date of Filing 30-Sep-2008
Name of Patentee JITSUBO CO., LTD.
Applicant Address 2-24-16, NAKACHO, KOGANEI-SHI, TOKYO
Inventors:
# Inventor's Name Inventor's Address
1 KIM, SHOKAKU C/O JITSUBO CO., LTD., 2-24-16, NAKACHO, KOGANEI-SHI, TOKYO 184-8588
2 CHIBA, KAZUHIRO C/O NATIONAL UNIVERSITY CORPORATION, TOKYO UNIVERSITY OF AGRICULTURE AND TECHNOLOGY, 8-1, HARUMICHO 3-CHOME, FUCHU-SHI,, TOKYO 183-8538
3 KONO, YUSUKE C/O JITSUBO CO., LTD., 2-24-16, NAKACHO, KOGANEI-SHI,, TOKYO 184-8588
PCT International Classification Number C07B 61/00,C07F 9/50
PCT International Application Number PCT/JP2007/052996
PCT International Filing date 2007-02-19
PCT Conventions:
# PCT Application Number Date of Convention Priority Country
1 2006-084019 2006-03-24 Japan