Dimethylformamide → 5-{4-[2-(5-Benzyloxymethyl-2-oxooxazolidin-3-yl)propoxy]benzyl}thiazolidine-2,4-dione

Participants

Reaction Steps

A procedure similar to that described in Example 4 was repeated, except that 200 mg of 5-{4-[2-(3-benzyloxy-2-hydroxypropylamino)propoxy]benzyl}thiazolidine-2,4-dione (prepared as described in Example 15), 73 mg of N,N'-carbonyldiimidazole and 20 ml of anhydrous dimethylformamide were used. The resulting crude product was purified by silica gel column chromatography, using a gradient elution method, with mixtures of ethyl acetate and hexane in ratios ranging from 2:1 to 3:1 by volume as the eluent, to give 160 mg of the title compound as a pale yellow glassy solid which was a mixture of a less polar diastereomer having an Rf value of 0.49 (on silica gel thin layer chromatography, using a 3:1 by volume mixture of ethyl acetate and hexane as the developing solvent) and a polar diastereomer having an Rf value of 0.38 (on silica gel thin layer chromatography, using a 3:1 by volume mixture of ethyl acetate and hexane as the developing solvent).

Provenance & Evidence