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TitleSynthesis of N-tert-butyloxycarbonyl-[2-(thien-2’-yl)benzoxazol-5-yl]-l-alanine methyl ester
Author(s)Costa, Susana P. G.
Raposo, M. Manuela M.
Esteves, Cátia Isabel Canavezes
Ferreira, Rosa Cristina Moutinho
KeywordsAmino acid
Nuclear magnetic resonance
Oxidative cyclization
Organic chemistry experiments
Laboratory classroom
Issue dateDec-2016
PublisherRoyal Society of Chemistry
CitationComprehensive Organic Chemistry Experiments for the Laboratory Classroom (COCELC), 2016, Cap. 185, Experiment 12.2.2, p 836-839.
Abstract(s)The aim of this work is the synthesis of a fluorescent heterocyclic amino acid, namely a benzoxazolyl- alanine, using simple experimental techniques and commercially available reagents. The starting aminotyrosine derivative and thiophene-2-carboxaldehyde will be combined in an oxidative cyclization to the oxazole in the presence of an oxidizing agent. The determination of the structure of the compound synthesized will be performed by 1H and 13C NMR spectroscopy. The experiment involves 3 sessions including the preparation of the intermediate N-tert-butyloxycarbonyl- 3-[(thien-2′-ylmethylene)amino]-l-tyrosine methyl ester and the preparation and purification of N-tert-butyloxycarbonyl[2-(thien-2′-yl)benzoxazol-5-yl]-l-alanine methyl ester.
TypeBook part
Publisher version
AccessRestricted access (Author)
Appears in Collections:CDQuim - Livros e Capítulos de Livros / Books and Book Chapters

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