Method for the enantioselective preparation of sulphoxide...

Details Method for the enantioselective preparation of sulphoxide... Method for the enantioselective preparation of sulphoxide...

C - Chemistry, Metallurgy

07

D

C07D 471/04 (2006.01) C07B 45/04 (2006.01) C07D 401/12 (2006.01)

Patent

CA 2520157

The invention relates to a method for the enantioselective preparation of substituted sulphoxide derivatives. The method comprises carrying out an enantioselective oxidation of a sulphide of general formula (I): A - CH2 - S - B (I), where A = a variously-substituted pyridyl nucleus and B = a heterocyclic group with a benzimidazole or imidazopyridyl nucleus, by means of an oxidising agent in the presence of a catalyst based on tungsten or vanadium and a chiral ligand, followed, where necessary, by salt formation with a base to give the sulphoxide: A - CH2 - SO - B (Ia). The above is of application to the enantioselective preparation of compounds such as the enantiomers of tenatoprazole and other comparable sulphoxides.

L'invention concerne un procédé de préparation énantiosélective de dérivés substitués de sulfoxydes. Le procédé consiste ô effectuer une oxydation énantiosélective d'un sulfure de formule générale (I) ci-après A - CH2 - S - B (I) dans laquelle A est un noyau pyridyle diversement substitué et B un reste hétérocyclique comportant un noyau benzimidazole ou imidazo-pyridyle, au moyen d'un agent oxydant en présence d'un catalyseur ô base de tungstène ou de vanadium et d'un ligand chiral, suivie le cas échéant d'une salification par une base, pour obtenir le sulfoxyde A - CH2 - SO - B (Ia). Application ô la préparation énantiosélective de composés tels que les énantiomères du ténatoprazole et d'autres sulfoxydes comparables.

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