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Preparation of optically active (acyloxy)alkyl esters from optically active O-acyl-α-hydroxy acids

✍ Scribed by Peter R Guzzo; Sean R Dinn; Jianhui Lu; Stefanie Oettinger-Loomis

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
79 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

Acyloxy)alkyl esters are commonly employed as prodrugs of carboxylic acid containing compounds. Several optically active (acyloxy)alkyl esters are prepared from a coupling and rearrangement reaction between optically active O-acyl-a-hydroxy acids and 3-chloroperoxybenzoic acid mediated by diisopropylcarbodiimide. The effect of temperature and solvent on the reaction is discussed. An application of the reaction to prepare a prodrug form of ibuprofen is described.

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