Fast and Convenient Synthesis of α-N-Protected Amino Acid Hydrazides

Giancarlo Verardo; Paola Geatti; Barbara Lesa

doi:10.1055/s-2004-837300

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Fast and Convenient Synthesis of α-N-Protected Amino Acid Hydrazides

Giancarlo Verardo*, Paola Geatti, Barbara Lesa
Dipartimento di Scienze e Tecnologie Chimiche, Università degli Studi di Udine, Via del Cotonificio 108, 33100 Udine, Italy
Fax: +39(0432)558803; e-Mail: giancarlo.verardo@uniud.it.;

Abstract

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Abstract

A fast, simple and convenient synthesis of α-N-protected amino acid hydrazides is reported. The procedure involves the reaction between hydrazine monohydrate and the mixed anhydride obtained from an α-N-protected amino acid and ethyl chloroformate. When methylhydrazine was used, the reaction showed a good selectivity, yielding a mixture of 1-acyl-1-methylhydrazine and 1-acyl-2-methylhydrazine in a ratio 87:13. In contrast, when the reaction was carried out with phenylhydrazine, only 1-acyl-2-phenylhydrazine was obtained. No significant difference in reactivity was observed with the different amino acids and N-protection introduced.

Key words

amino acids - hydrazides - regioselectivity - anhydrides - protecting groups

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