Collect. Czech. Chem. Commun. 1982, 47, 2291-2305

1-Aminocyclopropanecarboxylic acid and its derivatives

Zdenko Procházkaa, Miloš Buděšínskýa, Jorga Smolíkováa, Petr Trškab and Karel Jošta

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Prague Institute of Chemical Technology, 166 28 Prague 6


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.