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1. (WO1997021719) α, α-DIFLUORO-β-HYDROXY THIOL ESTERS AND THEIR SYNTHESIS

Pub. No.:    WO/1997/021719    International Application No.:    PCT/US1996/019867
Publication Date: Jun 19, 1997 International Filing Date: Dec 9, 1996
IPC: C07C 327/22
C07D 307/33
C07D 317/30
C07H 13/08
C07H 19/06
Applicants: ELI LILLY AND COMPANY
WEIGEL, John, A.
Inventors: WEIGEL, John, A.
Title: α, α-DIFLUORO-β-HYDROXY THIOL ESTERS AND THEIR SYNTHESIS
Abstract:
A process to make α, α-difluoro-β-hydroxy thiol esters of formula (IIIA), comprising reacting a difluoroethanethioate of formula (IVA), with a second reactant selected from the group consisting of aldehydes, ketones, acid halides and esters; in a solvent and in the presence of a strong base; with the proviso that the process is conducted in the absence of a catalyst and in the absence of a silyl containing compound is described and claimed. The α, α-difluoro-β-hydroxy thiol esters can be useful in the syntheses of organic compounds including gemcitabine hydrochloride.