US 2005/0038240 A1 · Processes for preparing 4'-azido-nucleoside derivatives

Abstract

A process for the preparation of a 4′-azido-2′,3′,5′-triacyl-nucleoside compound (I; B=B1; R1 is R1aCO— and R2 is R2aCO—) or a 4′-azidonucleoside compounds (I; B is B1 or B2 and R1 and R2 are hydrogen and acid addition salts thereof) wherein R1a and R2a are independently C1-10 alkyl or phenyl optionally substituted with 1 to 3 substituents selected from the group consisting of alkyl, alkoxy, halogen, nitro or cyano and R3 is selected from the group consisting of hydrogen, C1-6 alkyl, C1-3 haloalkyl and halogen, comprising contacting a 5′-iodo compound II with a peracid, R2aC(O)OOH, an acid R2aC(O)OH and a phase transfer catalyst and interconverting a uridine B1 to a cytosine B2. The present process provides the 4′-azidonucleosides safely and selectively in high purity with increased efficiency.

Claims9

Dependent claims

A process for the preparation of a 4′-azido-2′,3′,5′-triacyl-nucleoside compound according to formula I

comprising contacting a solution of a 5′-iodo compound II in a suitable solvent with a peracid, R2aC(O)OOH, an acid R2aC(O)OH and optionally a phase transfer catalyst wherein R1 is R1aCO—, R2 is R2a CO— and R1a and R2aare independently C1-10 alkyl or phenyl optionally substituted with 1 to 3 substituents selected from the group consisting of alkyl, alkoxy, halogen, nitro or cyano and R3 is selected from the group consisting of hydrogen, C1-6 alkyl, C1-3 haloalkyl and halogen.

Dependencies are inferred from the claim text.

Processes for preparing 4'-azido-nucleoside derivatives

Life of this patent

Processes for preparing 4'-azido-nucleoside derivatives

Life of this patent

Abstract

Claims9