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Paper | Special issue | Vol 82, No. 1, 2010, pp.543-554
Published online, 8th June, 2010
DOI: 10.3987/COM-10-S(E)25
An Efficient Synthesis of Methyl Esters of Heterocyclic α,β-Didehydro-α-amino Acid Derivatives

Franc Požgan, Klavdija Lukman, and Marijan Kočevar*

*Department of Organic Chemistry, Faculty of Chemistry and Chemical Technology, University of Ljubljana, Askerceva 5, P.O. Box 537, SI-1000 Ljubljana, Slovenia

Abstract

N-Benzoyl-protected α,β-didehydro-α-amino acid (DDAA) derivatives containing a pyrazole or an isoxazole ring at the β-position were transformed with diazomethane into the corresponding methyl esters. Applying this method, the double C=C bond of the DDAA derivatives was not affected, thus selectively giving the corresponding esters in good-to-excellent yields.