Processes for preparing 4'-azido nucleoside derivatives

Details Processes for preparing 4'-azido nucleoside derivatives Processes for preparing 4'-azido nucleoside derivatives

C - Chemistry, Metallurgy

07

H

C07H 19/067 (2006.01)

Patent

CA 2528294

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.

L'invention concerne une méthode de préparation d'un composé de 4'-azido-2',3',5'-triacyl-nucléoside (I;B=B1; R?1¿ est R?1a¿CO- et R?2¿ est R?2a¿CO-) ou un composé de 4'-azidonucléoside (I; B est B1 ou B2 et R?1¿ et R?2¿ sont hydrogène, et leurs sels d'addition acides). R?1a¿ et R?2a¿ sont indépendamment alkyle C¿1-10? ou phényle éventuellement substitué par 1 à 3 substituants sélectionnés dans le groupe constitué par alkyle, alcoxy, hydrogène, nitro ou cyano; et R?3¿ est sélectionné dans le groupe constitué par hydrogène, alkyle C¿1-6?, haloalkyle C¿1-3? et halogène. La méthode consiste à placer un composé de 5'-iodo II au contact d'un peracide (R?2a¿C(O)OOH) d'un acide (R?2a¿C(O)OH), et d'un catalyseur de transfert de phase, et à interconvertir une uridine B1 en cytosine B2. La méthode de l'invention produit de façon sûre et sélective des 4'-azidonucléosides de grande purité et d'efficacité accrue.

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