The chemistry of 4-mercaptoazetidin-2-ones. Part 1. Preparation and properties of (3R,4R)-4-mercapto-3-phenoxyacetamidoazetidin-2-one

Autor:	Neal F. Osborne
Rok vydání:	1980
Předmět:	Dimethyl acetylenedicarboxylate Acylation chemistry.chemical_compound chemistry Hexamethylphosphoramide Yield (chemistry) Organic chemistry Alkylation
Zdroj:	Journal of the Chemical Society, Perkin Transactions 1. :146
ISSN:	1364-5463 0300-922X
DOI:	10.1039/p19800000146
Popis:	(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).
Databáze:	OpenAIRE
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