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Facile synthesis of N-protected amino acid assisted by microwave irradiation
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Biochemistry and Organic Chemistry.
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
Abstract [en]

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.
Keyword [en]
amino acid ester, microwave synthesis, amino alcohol
National Category
Chemical Sciences
URN: urn:nbn:se:uu:diva-109081DOI: 10.1007/s10989-008-9134-3ISI: 000258840200004OAI: oai:DiVA.org:uu-109081DiVA: diva2:248810
Available from: 2009-10-09 Created: 2009-10-09 Last updated: 2009-10-09Bibliographically approved

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