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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

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

Bruzgulienė Jolita J   Račkauskienė Greta G   Bieliauskas Aurimas A   Milišiūnaitė Vaida V   Dagilienė Miglė M   Matulevičiūtė Gita G   Martynaitis Vytas V   Krikštolaitytė Sonata S   Sløk Frank A FA   Šačkus Algirdas A  

Beilstein journal of organic chemistry 20220112


A convenient and efficient synthesis of novel achiral and chiral heterocyclic amino acid-like building blocks was developed. Regioisomeric methyl 5-(<i>N</i>-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, <sup>1</sup>H, <sup>13</sup>C, and <sup>15</sup>N NMR spectroscopy, HRMS, and sin  ...[more]

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