Multicomponent Synthesis of a N-Protected α-Amino Ester: Ethyl 2-((4-Methoxyphenyl)amino)-3-phenylpropanoate

• Autores: Erwan Le Gall, Antoine Pignon
• Localización: Journal of chemical education, ISSN 0021-9584, Vol. 89, Nº 9, 2012, págs. 1190-1193
• Idioma: inglés
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• Resumen

  • This laboratory experiment describes the preparation of a N-protected phenylalanine ethyl ester by a zinc-mediated Mannich-like multicomponent reaction between benzyl bromide, p-anisidine, and ethyl glyoxylate. The one-step reaction involves the in situ metallation of benzyl bromide into a benzylzinc reagent and its addition onto imine (Barbier conditions). The multicomponent procedure is suitable for a 4-to-5 h undergraduate organic laboratory.