Regioselective synthesis of methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates as new amino acid-like building blocks.

ABSTRACT: A convenient and efficient synthesis of novel achiral and chiral heterocyclic amino acid-like building blocks was developed. Regioisomeric methyl 5-(N-Boc-cycloaminyl)-1,2-oxazole-4-carboxylates were prepared by the reaction of β-enamino ketoesters (including azetidine, pyrrolidine or piperidine enamines) with hydroxylamine hydrochloride. Unambiguous structural assignments were based on chiral HPLC analysis, ¹H, ¹³C, and ¹⁵N NMR spectroscopy, HRMS, and single-crystal X-ray diffraction data.

SUBMITTER: Bruzguliene J 

PROVIDER: S-EPMC8767561 | biostudies-literature | 2022

REPOSITORIES: biostudies-literature