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KMID : 1059519940380050372
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Journal of the Korean Chemical Society
1994 Volume.38 No. 5 p.372 ~ p.376
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A Study on the Reactivites of a Penicillin-derived 4-Mercaptoazetidin-2-one
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Chung Kyoo-Hyun
Kim Hyung-Tae
Heo Hong-Il
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Abstract
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The penicillin-derived 4-mercaptoazetidin-2-one(2a) was unstable in basic media, but it reacted with electrophiles such as acetyl chloride, methyl chloroformate, ethyl iodoacetate, diethyl azodicarboxylate in the presence of triethylamine or pyridine to give the products such as S-acetyl, S-methoxycarbonyl, S-ethoxycarbonylmethyl, and S-diethoxycarbonylhydrazino compounds. However S-methylation could not be done with methyl iodide, but with diazomethane. The reactivity of isomer 3a toward electrophiles was almost the same as that of compound 2a.
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