m-Chloroperbenzoic acid → HCID 13649352, compound

Participants

Reaction Steps

To a solution of 357 mg of (1R,4R)-3-benzoyl-4-[(R)-α-methylbenzylcarbamoyl]-1-oxothiazolidine (prepared as described in Example 25 or 28 ) in 10 ml of methylene chloride were added 203 mg of 85% m-chloroperbenzoic acid, and the mixture was stirred at room temperature for 20 hours. The reaction mixture was then washed, in turn, with 30 ml of a 4% aqueous solution of sodium bicarbonate and with 30 ml of water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to leave an oil, which was then subjected to column chromatography through 80 g of silica gel, eluted with a 97.5:2.5 by volume mixture of methylene chloride and ethanol, to give an oil. This oil was crystallized by the addition of benzene to give 266 mg of the title compound in the form of crystals. The physical properties of these crystals were identical with those of the compound obtained as described in Example 27.

Provenance & Evidence