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US 10,030,043 B2Granted
Method for the synthesis of clofarabine
AssigneeSynbias Pharma AG
InventorsAlexander Zabudkin, Victor Matvienko, Iaroslav Matviienko, Volodymyr Sypchenko
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Abstract
The present invention relates to a method for the high yield production of the anticancer nucleoside clofarabine, the method comprising the preparation of 2-chloroadenosine by enzymatic transglycosylation between 2-chloroadenine and nucleosides, benzoylation, isomerization, sulfonate ester formation, fluorination, and deprotection.
Claims8
Method for the production of clofarabine, comprising:
- (a) preparing 2-chloroadenosine by enzymatic transglycosylation between 2-chloroadenine and a compound of formula 1,
- wherein, R1 is purine or pyrimidine base of formula 2 or formula 3, respectively,
- wherein R2 and R3 are independently selected from the group consisting of —H, —NH2, —OH, and —CH3;
- and
- R4 is selected from the group consisting of —H and —CH3;
- (b) partially protecting the hydroxyl groups of 2-chloroadenosine to obtain a mixture of a compound of formula 4 and a compound of formula 5,
- wherein R5 is independently a hydroxyl protecting group;
- (c) isomerizing the compound of formula 4 to the compound of formula 5;
- (d) preparing a compound of formula 6 from the compound of formula 5,
- wherein OR6 is a leaving group;
- (e) fluorinating the compound of formula 6 to a compound of formula 7;
- and
- (f) deprotecting the compound of formula 7 to obtain clofarabine.
10 more elements
Dependencies are inferred from the claim text.