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

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 seri...

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Bibliographic Details
Published in:Synlett 2017-09, Vol.28 (14), p.1729-1732
Main Authors: Patil, Pravin C., Luzzio, Frederick A.
Format: Article
Language:English
Subjects:
cluster
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0036-1588510