2-thiacephems and (5r) penems derivatives

C - Chemistry – Metallurgy – 07 – D

Patent

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C07D 499/00 (2006.01) C07D 205/09 (2006.01) C07D 417/12 (2006.01) C07D 499/88 (2006.01) C07D 513/04 (2006.01) C07F 7/10 (2006.01) C07F 7/18 (2006.01)

Patent

CA 1221358

ABSTRACT A new process is described for the preparation of (5R)-penem derivatives of the general formula I: Image I wherein R1 represents a hydrogen atom or an organic group; R2 represents a hydrogen atom or a carboxy protecting group and Y represents a hydrogen or halogen atom or an organic group. A 2-thiacephem derivative of the general formula II: Image II wherein R1, R2 and Y have the meanings/given above is oxidized by means of organic peracids to the corresponding sulphone of the general formula III: Image III which is subsequently submitted to a desulphurative ring contraction by extrusion of SO2 to give exclusively the desired (5R)-penem derivatives of the general formula I.

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