Carbamoyl Azides of α-N-Protected Amino Acids: A Fast and Simple One-Pot Synthesis

Giancarlo Verardo; Elisa Bombardella; Paola Geatti; Paolo Strazzolini

doi:10.1055/s-2008-1032029

PAPER

Carbamoyl Azides of α-N-Protected Amino Acids: A Fast and Simple One-Pot Synthesis

Giancarlo Verardo*, Elisa Bombardella, Paola Geatti, Paolo Strazzolini
Department of Chemical Sciences and Technologies, University of 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 and simple one-pot synthesis of carbamoyl azides of α-N-protected amino acids is reported. The procedure involves the reaction between sodium azide and the mixed anhydride obtained from an α-N-protected amino acid and isobutyl chloroformate, in the presence of KH₂PO₄. The reaction rate was influenced by the nature of both the α-N-protection and the amino acid side chain. Surprisingly, tert-butyloxycarbonyl (α-N-Boc) and benzyloxycarbonyl (α-N-Cbz) protected proline afforded the corresponding isocyanates instead of the expected carbamoyl azides.

Key words

α-N-protected amino acids - sodium azide - carbamoyl azide - mixed anhydride - Curtius rearrangement

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References

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