FIELD: organic chemistry, chemistry of nucleosides, biochemistry. SUBSTANCE: invention relates to the improved method of synthesis of 3'-azido-2', 3'-dideoxythymidine (azidothymidine) used in medicine as an antiviral preparation for treatment of patients with acquired immunodeficiency syndrome (AIDS). Method involves azidation of 5'-O-benzoyl-2,3'-anhydrothymidine with alkylammonium azides in aprotonic organic solvent (a mixture of dipolar solvent with 1,4-dioxane) followed by isolation of the end substance by the known method. Process is carried out at volume ratio dipolar solvent : 1,4-dioxane = (1.5-1)-(4.0-1) and at 100-110 C. The yield is 85-87%. The use of dipolar solvent in mixture with 1,4-dioxane ensures to increase the yield of the end product and decrease impurity content in it. EFFECT: improved method of synthesis, increased yield and purity. 3 cl, 1 tbl, 1 ex
Title | Year | Author | Number |
---|---|---|---|
METHOD OF PREPARING 3'-AZIDO-2',3'-DIDEOXYTHYMIDINE | 1997 |
|
RU2130942C1 |
3'-(5-R-TETRAZOLE-2-YL)-THYMIDINES SHOWING ANTIVIRAL ACTIVITY AND METHOD OF THEIR SYNTHESIS | 1993 |
|
RU2124020C1 |
METHOD OF PHOSPHONATION OF 2′,3′-DIDESOXYNUCLEOSIDES | 1997 |
|
RU2133754C1 |
METHOD FOR PRODUCING 3′-AZIDO-2′,3′--DIDESOXYTHYMIDINE | 1994 |
|
RU2102399C1 |
METHOD OF AZIDOTHYMIDINE SYNTHESIS | 1992 |
|
RU2034848C1 |
METHOD OF SYNTHESIS 2'-DEOXYXYLOTHYMIDINE, DERIVATIVES OF D-XYLOFURANOSE, DERIVATIVES OF XYLOTHYMIDINE | 1994 |
|
RU2108339C1 |
5-H-PHOSPHONATE-3-AZIDO-3-DESOXYTTEMIDINE SALTS WHICH ARE SPECIFIC INHIBITORS VICH-1 AND VICH-2 | 1996 |
|
RU2106353C1 |
METHOD FOR PRODUCTION OF 5'-BENZOYL-2,3'-ANHYDROXYL THYMIDINES | 1992 |
|
RU2074862C1 |
METHOD OF NUCLEOSIDE LINKAGE BY 3'--5'-INTERNUCLEOTIDE SILYL UNIT | 1991 |
|
RU2079508C1 |
METHOD OF PRODUCING 5'-AMINOCARBONYLPHOSPHONATES OF NUCLEOSIDES AND METHOD OF PRODUCING ACYL CHLORIDE OF TRIMETHYLSILYL ETHER OF ETHOXYCARBONYLPHOSPHONIC ACID | 2010 |
|
RU2446169C2 |
Authors
Dates
1999-08-27—Published
1997-07-11—Filed