An Efficient Synthesis of Aryl Phenaceturates Using Acid Catalyzed Dicyclohexylcarbodiimide Esterification and Transient N-trent-Butoxycarbonylation

Daniel Cabaret; Jie Liu; Michel Wakselman

doi:10.1055/s-1994-25507

Synthesis 1994; 1994(5): 480-482
DOI: 10.1055/s-1994-25507

short paper

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An Efficient Synthesis of Aryl Phenaceturates Using Acid Catalyzed Dicyclohexylcarbodiimide Esterification and Transient N-trent-Butoxycarbonylation

Daniel Cabaret^* , Jie Liu, Michel Wakselman

^*CNRS-CERCOA, 2 rue Henri Dunant, F-94320 Thiais, France

Abstract

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Application of the Holmberg procedure (DCC/pyridine/p-TSA_cat) improves the yield of the direct condensation of phenols with phenylacetylglycine (1). Moreover, N-tert-butoxycarbonylation of 1 impedes an intramolecular reaction leading to an oxazolone, and allows the formation of stable aryl N-Boc phenaceturates. Then, mild cleavage of the Boc group with four equivalents of trifluoroacetic acid furnishes the aryl phenylacetylglycinate. This indirect method is more efficient than its direct analog in the case of phenols possessing electron-withdrawing substituents.

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