Synlett 2017; 28(14): 1729-1732
DOI: 10.1055/s-0036-1588510
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© Georg Thieme Verlag Stuttgart · New York

Unnatural Amino Acid Derivatives through Click Chemistry: Synthesis of Triazolylalanine Analogues

Pravin C. Patil
Department of Chemistry, University of Louisville, 2320 South Brook Street, Louisville, Kentucky 40292, USA   Email: Faluzz01@louisville.edu
,
Frederick A. Luzzio*
Department of Chemistry, University of Louisville, 2320 South Brook Street, Louisville, Kentucky 40292, USA   Email: Faluzz01@louisville.edu
› Author Affiliations
This work was financially supported by the NIH/NIDCR through grant 1RO1DEO23206
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Publication History

Received: 08 May 2017

Accepted after revision: 26 June 2017

Publication Date:
24 July 2017 (online)


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Published as part of the ISHC Conference Special Section

Abstract

A novel tert-butyl 2-(1-oxoisoindolin-2-yl)acetate derivative is selectively alkylated with propargyl bromide in the presence of lithium hexamethyldisilazide. After removal of the tert-butyl protecting group, the resulting N-isoindolinyl (ethynylalanine) derivative is reacted with a series of azides under ‘click conditions’. The click reactions afford an array of N-isoindolinyl- 1,2,3-triazolylalanine derivatives as the free carboxylic acids. Following esterification, the N-isoindolinone protecting group is then transformed into the more easily removable phthaloyl group by selective oxidation at the benzylic position.

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