Studies related to β-lactam antibiotics. IX. Alcoholysis of a 4-oxa-1-azabicyclo[3.2.0]heptane-3,7-dione

Article abstract of DOI:10.1248/cpb.31.4539

Thermal reactions of (2R, 5S, 6S)-2-(1-methylethenyl)-6-phenylacetamido-4-oxa-1-azabicyclo[3.2.0]heptane -3,7-dione (1) with alcohols gave 2-phenylmethyl-4-→N-[(1R)-1-carboxy-2-methylprop-2-enyl]←carbamoyloxazol e (2a), (3S, 4S)-4-alkoxy-1-[(1R)-1-carboxy-2-methylprop-2-enyl]-3-phenylacetamidoazeti din-2-ones (3a, c), and (2S)-N-[(1R)-1-carboxy-2-methylprop-2-enyl]-3,3-dialkoxy-2-phenylacetamido propionamides (4a, c), probably via an intramolecular ring transformation of 1 into (1S, 5R)-3-phenylmethyl-6-[(1R)-1-carboxy-2-methylprop-2-enyl]-4-oxa-2,6-diazab icyclo[3.2.0]hept-2-en-7-one (5a) in the initial stage of the reaction.

Full text of DOI:10.1248/cpb.31.4539

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