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Paper | Special issue | Vol 28, No. 2, 1989, pp.1061-1076
Published online, 1st January, 1970
DOI: 10.3987/COM-88-S127
Synthesis of 3-(Alkyl and Aryl)thio-2-isocephems

Jozsef Aszodi,* Jean-François Chantot, Jeannine Collard, and Georges Teutsch

*Centre de Recherche ROUSSEL-UCLAF, 102-111, route de Noisy, 93230 Romainville, France

Abstract

Synthesis of 3-S-substituted isocephems has been carried out in a convergent way using readily available intermediates such as 4-mercaptomethylazetidinone 3 and chloropyruvates 4 prepared by the reaction of sulfenyl chlorides with t-butyl diazopyruvate. During the synthesis, mild acid catalyzed decarboxylation of the β-carboxy ketene-dithioacetal moiety was observed as a side-reaction.