Enantioselective preparation of benzimidazole derivatives...

Details Enantioselective preparation of benzimidazole derivatives... Enantioselective preparation of benzimidazole derivatives...

C - Chemistry, Metallurgy

07

D

C07D 401/12 (2006.01) C07D 235/28 (2006.01)

Patent

CA 2634138

The invention relates to a new process for preparing benzimidazole derivatives having a chiral sulfoxide group in enantiomerically pure form or in a form in which one of the two enantiomers is present in an increased quantity over the other enantiomer. The invention likewise relates to a process for preparing the salts of the individual enantiomers of the benzimidazole derivatives with a chiral sulfoxide group. The invention relates in particular to a process for preparing the S-enantiomer of omeprazole (also known as esomeprazole) and the salts thereof, more particularly the zinc salt of the S-enantiomer of omeprazole. In the new process a prochiral sulfide is oxidized in an organic solvent with an oxidizing agent in the presence of a titanium(IV) complex.

L'invention concerne un nouveau procédé de fabrication de dérivés de benzimidazole avec un groupement sulfoxyde chiral sous forme énantiomérique ou sous une forme enrichie en un des deux énantiomères par rapport à l'autre énantiomère. L'invention concerne également un procédé de fabrication du sel de l'énantiomère isolé du dérivé de benzimidazole avec un groupement sulfoxyde chiral. L'invention concerne notamment un procédé de fabrication de l'énantiomère S de l'oméprazol (également connu sous le nom d'ésoméprazol) et de son sel, notamment du sel de zinc de l'énantiomère S de l'oméprazol. Selon le nouveau procédé, un sulfure prochiral est oxydé dans un solvant organique par un agent d'oxydation en présence d'un complexe de titane (IV).

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