Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies Related to β-Lactam Antibiotics. IX. Alcoholysis of a 4-Oxa-1-azabicyclo [3.2.0] heptane-3, 7-dione
酒向 孫市明楽 一己広田 耕作牧 敬文
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1983 年 31 巻 12 号 p. 4539-4542

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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] carbamoyloxazole (2a), (3S, 4S)-4-alkoxy-1-[(1R)-1-carboxy-2-methylprop-2-enyl]-3-phenylacetamidoazetidin-2-ones (3a, c), and (2S)-N-[(1R)-1-carboxy-2-methylprop-2-enyl]-3, 3-dialkoxy-2-phenylacetamidopropionamides (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-diazabicyclo [3.2.0] hept-2-en-7-one (5a) in the initial stage of the reaction.
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