1-Aminocyclopropanecarboxylic acid and its derivatives

Abstract

Action of strongly basic reagents on methyl Nα-benzyloxycarbonylamino-γ-bromobutyrate leads to 1-aminocyclopropanecarboxylic acid derivatives whose structure was determined by 1H NMR, 13C NMR and IR spectroscopy. According to IR spectroscopy, the urethane CO-NH group in crystalline methyl 1-benzyloxycarbonylaminocyclopropanecarboxylate exists in the cis(E) conformation which on dissolution is transformed into the trans(Z) form. NMR spectroscopy showed that the acid-catalyzed esterification of α-amino-γ-bromobutyric acid is accompanied by replacement of the covalently bonded bromine by chlorine.