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

(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-α-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.