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The Chemistry of 4-Mercaptoazetidin-2-ones. Part 1. Preparation and Properties of (3R,4R)-4-Mercapto-3-phenoxyacetamidoazetidin-2-one
Osborne, Neal F.
, p. 146 - 149 (2007/10/02)
(3R,4R)-4-Mercapto-3-phenoxyacetamidoazetidin-2-one (4) has been prepared in good yield from the penicillin V-derived thiazoline-azetidinone (1).Alkylation and acylation led exclusively to S-substituted azetidinones.Reaction with dimethyl acetylenedicarboxylate in hexamethylphosphoramide gave, in addition to the expected dimethoxycarbonylvinylthioazetidinone (15), the C-4-epimer (18).The latter probably arises via the intermediacy of the azetinone (16).
