Tetrahedron letters

Mild regeneration of the carboxylic group of amino acid alkyl esters by aqueous methanolic sodium hydrogen carbonate via 5-oxazolidinones

P Allevi, M Anastasia

Index: Allevi, Pietro; Anastasia, Mario Tetrahedron Letters, 2003 , vol. 44, # 41 p. 7663 - 7665

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Citation Number: 6

Abstract

We report herein a successful protocol for a two-step cleavage of easily accessible methyl esters of Cbz-, Fmoc- and Boc-protected amino acids. This protocol consists of two simple reactions: the preparation of 5-oxazolidinones by acid-catalyzed condensation of protected amino esters, and their hydrolysis by treatment with sodium hydrogen carbonate in aqueous methanol (Scheme 1). Under these very mild conditions the regeneration of the amino acid ...