Ultrasound and ZnCl2 Promoted Synthesis of Phthaloyl Derivatives of α-Amino Carboxamides

J. Richard Casimir; Gilles Guichard; Jean-Paul Briand

doi:10.1055/s-2001-9756

Synthesis 2001; 2001(1): 0075-0080
DOI: 10.1055/s-2001-9756

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Ultrasound and ZnCl₂ Promoted Synthesis of Phthaloyl Derivatives of α-Amino Carboxamides

J. Richard Casimir^* , Gilles Guichard, Jean-Paul Briand

^*Laboratoire de Chimie Immunologique, UPR 9021 CNRS, Institut de Biologie, Moléculaire et Cellulaire, 15 rue René Descartes, F-67084 Strasbourg cedex, France; Fax +33(3)88 61 06 80; E-mail: R.Casimir@ibmc.u-strasb.fr

Abstract

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A new, one-step and racemization-free synthesis of phthaloyl derivatives of α-amino carboxamides is described. Under ultrasound, α-amino carboxamides and dipeptide derivatives react with monomethyl phthalate in the presence of BOP, ZnCl₂ and i-Pr₂NEt to afford the corresponding N ^α-phthaloyl α-amino carboxamides or dipeptides in good to excellent yields. Cyclization of the intermediate N ^α-[(o-methoxycarbonyl)benzoyl]amino carboxamides to the desired products was very slow when the reaction was conducted either in the absence of ZnCl₂ and/or without sonication, but the process was greatly accelerated when both ZnCl₂ and ultrasound were used.

phthaloyl protection - zinc chloride - sonochemistry - α-amino carboxamides - monomethylphthalate - cyclization - peptides

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