Isomerization and Decomposition Products of Methicillin1

DA Johnson, CA Panetta

Index: Johnson,D.A.; Panetta,C.A. Journal of Organic Chemistry, 1964 , vol. 29, p. 1826 - 1830

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Citation Number: 12

Abstract

In weakly acidic media, methicillin (1) isomerizes to 3, 6-dimethoxyph~ nylpenicillenic acid (2) which then decomposes spontaneously to 2, 6-dimethoxyphenylpenicilloic acid (3), 2, 6- dimethoxyphenylpenilloic acid (4), 2, 6-dimethoxghippuric acid (S), N-formyl-o-penicillamine (6), and 3.10-bis (2, 6-dimethoxybenzamido)-6, 6, 13, 13-tetramethyl-2, 9-diox0-5, 12-dithia- l, 8-diazatricyclo [9.3. 0.0~~~] tetradecane-7, 14-dicarbnxylic acid (7, see Scheme