Process for preparing optically active penems

C - Chemistry – Metallurgy – 07 – D

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C07D 499/00 (2006.01) C07D 205/08 (2006.01) C07D 499/88 (2006.01) C07F 7/18 (2006.01) C07F 9/568 (2006.01)

Patent

CA 1215705

ABSTRACT OF THE DISCLOSURE Processes for the preparation of a penem derivative of formula I Image wherein n = 0 or 1; R is a carboxy protecting group or H; R1 is hydrogen, a hydrocarbon group substituted or unsubstituted, or lower alkoxy; and R2 is hydrogen, C1 - C5 alkyl, carbamoyl N-substituted by lower alkyl or unsubstituted, or an acyl group; and the pharmaceutically acceptable salts thereof. These processes allow one to prepare stereospecifically only 5R derivatives, and are characterized by R2-introduction at a very late stage in the synthesis, thereby enabling a great number of compounds of formula I to be prepared. Penem derivatives are useful antibacterial agents.

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