Process for preparing 2′-deoxy-2′,...

Details Process for preparing 2′-deoxy-2′,... Process for preparing 2′-deoxy-2′,...

2011-08-09

2011-08-09

Crane, Lawrence E (Department: 1623)

Organic compounds -- part of the class 532-570 series

Organic compounds

Carbohydrates or derivatives

C536S028500

Reexamination Certificate

active

07994310

ABSTRACT:
Disclosed is a method for preparing 2′-deoxy-2′,2′-difluorocytidine of Formula I comprising, preparing an optically pure 3R-hydroxypropane amide compound of Formula VIII from an optical ester compound of Formula IX using an optically active chiral amine, preparing an optically pure D-erythro-2,2-difluoro-2-deoxy-1-oxoribose compound of Formula V from the compound of Formula VIII, glycosylating the compound of Formula V with a nucleobase to prepare the 2′-deoxy-2′,2′-difluorocytidine of Formula I as a β-nucleoside. With the present invention, it is possible to prepare an optically pure compound of Formula I in a high purity and a high yield. In the Formulae, R1and R2are protecting groups and are each independently benzoyl, 4-methylbenzoyl, 3-methylbenzoyl, 4-cyanobenzoyl, 3-cyanobenzoyl, 4-propylbenzoyl, 2-ethoxybenzoyl, 4-t-butylbenzoyl, 1-naphthoyl or 2-naphthoyl, R3, R4and R7are each independently C1-C3alkyl, R5is methyl or ethyl, R6is hydrogen, methyl or methoxy.

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