Facile synthesis of N-protected amino acid assisted by microwave irradiation
2008 (English)In: International journal of peptide research and therapeutics, ISSN 1573-3149, Vol. 14, no 3, 219-222 p.Article in journal (Refereed) Published
A highly efficient and safe methodology for synthesis of various N-protected amino acid ethyl esters have been established in this study. This methodology employs orthoesters as both esterification reagent and solvent for protected amino acids. The reactions were carried out under microwave irradiation in neutral conditions for only 2 min, resulting in highly pure crude products in most cases. This strategy works with a variety of N-protecting groups, such as acid labile protecting group: BOC and tBu, base labile protecting group: Fmoc, hydrogenation labile protecting group: Z and Na/NH3 labile protecting group: Tos, thus providing facile access to numerous valuable building blocks for solid phase synthesis. Further reduction of the crude protected amino acid ethyl ester by sodium borohydride under mild conditions led to the corresponding protected beta-amino alcohols with excellent yield, as demonstrated by three examples.
Place, publisher, year, edition, pages
2008. Vol. 14, no 3, 219-222 p.
amino acid ester, microwave synthesis, amino alcohol
IdentifiersURN: urn:nbn:se:uu:diva-109081DOI: 10.1007/s10989-008-9134-3ISI: 000258840200004OAI: oai:DiVA.org:uu-109081DiVA: diva2:248810