.alpha., .alpha.-difluoro-.beta.-hydroxy thiol esters and...

C - Chemistry – Metallurgy – 07 – H

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C07H 19/073 (2006.01) C07C 327/22 (2006.01) C07D 317/30 (2006.01)

Patent

CA 2239891

A process to make .alpha., .alpha.-difluoro-.beta.-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 .alpha., .alpha.-difluoro-.beta.-hydroxy thiol esters can be useful in the syntheses of organic compounds including gemcitabine hydrochloride.

L'invention se rapporte à un procédé de fabrication de .alpha.,.alpha.-difluoro-.beta.-hydroxy thiol esters de la formule (IIIA), ce procédé consistant à faire réagir un difluoroéthanethioate de la formule (IVA) avec un second réactif sélectionné dans le groupe comprenant des aldéhydes, cétones, halogénures d'acides et esters dans un solvant et en présence d'une base forte, à condition que le procédé soit effectué en l'absence d'un catalyseur et en l'absence d'un composé contenant un silyle. Les .alpha.,.alpha.-difluoro-.beta.-hydroxy thiol esters peuvent être utilisés dans les synthèses de composés organiques comprenant l'hydrochlorure de gemcitabine.

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