Publicação
Synthesis of N-tert-butyloxycarbonyl-[2-(thien-2’-yl)benzoxazol-5-yl]-l-alanine methyl ester
| Resumo: | 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. |
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| Autores principais: | Costa, Susana P. G. |
| Outros Autores: | Raposo, M. Manuela M.; Esteves, Cátia Isabel Canavezes; Ferreira, Rosa Cristina Moutinho |
| Assunto: | Amino acid (benz)oxazole Chromatography Nuclear magnetic resonance Oxidative cyclization Thiophene Organic chemistry experiments Laboratory classroom Ciências Naturais::Ciências Químicas |
| Ano: | 2016 |
| País: | Portugal |
| Tipo de documento: | capítulo de livro |
| Tipo de acesso: | acesso restrito |
| Instituição associada: | Universidade do Minho |
| Idioma: | inglês |
| Origem: | RepositóriUM - Universidade do Minho |
| Resumo: | 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. |
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