| Title of Invention | A PROCESS FOR THE PREPARTION OF ORGANIC AZIDES |
|---|---|
| Abstract | A process for the preparation of organic azide the addition of an azide fuction to an organic compound in which process a mixture is prepared by adding an epoxide-derivative of the organic compound and an alkali metal azide salt to a solvent is described. The mixture is heated to a reaction temperature at which the epoxide-derivative and the azide can react to form an azide derivative of the organic compound. An amount,near equimolar to the epoxide derivative,of a (1-6c)alky-(2-4c)carboxylic acid ester having a boiling point above the reaction temperature is added to the mixture before and/or during the reaction. |
| Full Text | methylethyliclene)-p-D-glucopyranosyl]-p-D-mannopyranose are more preferred. The further preferred use of the process is for the formation of 2-azido-2-deoxy-pyranose, which is a precursor for a glycosamine moiety in a glycosaminoglycan with antithrombotic properties. Alkali metal azides which can be used are lithium azide, potassium azide and sodium azide, whereby sodium azide is preferred. Many different types of solvent can be used in the process, for example ethanol, acetonitril, dimethylsulfoxide or hexamethylene. Preferred is the use of a polar aprotic solvent, which is a solvent which is miscible with water, has a high dielectric constant (ε>15) and is incapable of donating hydrogen for formation of hydrogen bridges. Preferred solvents are dimethylformamide, N-methylpyrrolidinone or dimethylacetamide. N-methylpyrrolidinone is most preferred when carbohydrates are azidised. Preferably, water is added to the solvent in order to allow for a higher concentration of the water soluble alkali metal azide salt in the reaction mixture. A considerable amount of water, up to an equal volume to the organic solvent, can be present in the reaction mixture. The addition reaction can usually take place at reaction temperatures ranging from 60-120 °C and preferably at 110 °C. The completion of the addition reaction can be determined by measurement of components in the mixture with methods generally known to the skilled person. The reaction can last from one hour to several days depending upon the reactivity of the organic epoxide and on the various compounds in the mixture. When no substantial increase in the amount of organic azide, formed during the reaction, is observed or the amount of products from unwanted side reactions increases, the reaction is completed. Accordingly the present invention provides a process for preparation of an organic azide by the addition of an azide function to an organic compound, in which process an epoxide-derivative of the organic compound and an alkali metal azide salt react in a solvent to form an azide derivative of the organic compound, wherein an amount, near equimolar to the epoxide derivative, of a (l-6C)alkyl-(2-4C)carboxylic acid ester having a boiling point above the reaction temperature is added to the reaction mixture before and/or during the reaction. The following example is described for illustration of the invention. WE CLAIMS: 1. A process for preparation of an organic azide by the addition of an azide function to an organic compound, in which process an epoxide-derivative of the organic compound and an alkali metal azide salt react in a solvent to form an azide derivative of the organic compound, wherein an amount, near equimolar to the epoxide derivative, of a (l-6C)alkyl-(2-4C)carboxylic acid ester having a boiling point above the reaction temperature is added to the reaction mixture before and/or during the reaction. 2. The process according to claim 1, wherein the epoxide-derivative of the organic compound is selected from stryrene oxide, 2,3-epoxybutane, indene oxide, and an epoxy derivative of a carbohydrate. 3. The process according to claim 2, wherein the epoxide-derivative of the organic compound is an epoxy derivative of a carbohydrate. 4. The process according to claim 3, wherein the epoxide derivative of a carbohydrate is l,6:2,3-dianhydro-4-O-phenylmethyl-B-D-mannopyranose or l,6:2,3-dianhydro-4-O-[2,3-bis-O-phenylmethyl-4,6-O-phenylmethylidene-B-D-glucopyranosyl]-B-D-mannopyranose or l,6:2,3-dianhydro-4-O-[2,3-bis-O-phenylmethyl-4, 6-O-(l-methylethylidene)-B-D-glucopyranosyl]-B-D-mannopyranose. 5. The process according to anyone of claims 1 to 4, wherein the reaction temperature is between 60 and 120°C. 6. The process according to anyone of claims 1 to 5, wherein the ester is butylacetate. 7. The process according to anyone of claims 1 to 6, wherein water is added to the reaction mixture in an amount of at most equal to the volume of the solvent. 8. A process for preparation of an organic azide by the addition of an azide function to an organic compound substantially as herein described with reference to the accompanying drawings. |
|---|
053-mas-2000-correspondence others.pdf
053-mas-2000-correspondence po.pdf
053-mas-2000-description complete filed.pdf
053-mas-2000-description complete grand.pdf
053-mas-2000-other document.pdf
| Patent Number | 210242 | |||||||||
|---|---|---|---|---|---|---|---|---|---|---|
| Indian Patent Application Number | 53/MAS/2000 | |||||||||
| PG Journal Number | 50/2007 | |||||||||
| Publication Date | 14-Dec-2007 | |||||||||
| Grant Date | 25-Sep-2007 | |||||||||
| Date of Filing | 24-Jan-2000 | |||||||||
| Name of Patentee | M/S. SANOFI-SYNTHELABO | |||||||||
| Applicant Address | 174 AVENUE DE FRANCE,75013 PARIS, | |||||||||
Inventors:
|
||||||||||
| PCT International Classification Number | C07B43/00 | |||||||||
| PCT International Application Number | N/A | |||||||||
| PCT International Filing date | ||||||||||
PCT Conventions:
|
||||||||||