DL-Cyclocanaline (cyclohomoserine) and related compounds

Abstract

DL-Cyclocanaline (4-aminotetrahydro-1,2-oxazin-3-one) hydrochloride, the higher homologue of the antibiotic cycloserine, has been prepared from canaline (2-amino-4-amino-oxybutyric acid) dihydrochloride. Its chemical and physical properties are reported. α-N-Triphenylmethyl- and α-N-benzoyl-cyclocanaline have been synthesised by N-tritylation of the oxa-lactam and by cyclisation of the α-benzamidocanaline ester derivative, respectively. Derivatives of DL-canaline ester bearing various protecting groups on the amino- and amino-oxy-groups were obtained; N-benzyloxycarbonylhydroxylamine was utilised for the introduction of the amino-oxy group.