Mechanism of hydrolysis of benzamidomethyl derivatives of phenols and its implications for prodrug design

JJ Getz, RJ Prankerd, KB Sloan

Index: Getz, John J.; Prankerd, Richard J.; Sloan, Kenneth B. Journal of Organic Chemistry, 1992 , vol. 57, # 6 p. 1702 - 1706

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Citation Number: 21

Abstract

A series of 0-benzamidomethyl derivatives of phenols was synthesized, and their rates of hydrolysis were investigated. The hydrolyses of the compounds follow pseudo-first-order kinetics resulting in quantitative and rapid regeneration of the phenol. The rates of hydrolysis were shown to be dependent on phenol nucleofugicity as well as the pKa of the amide. The mechanism of hydrolysis apparently involves an elimination of the phenol anion from the ...