Hydrochloric Acid → 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoic acid

Participants

Reaction Steps

400 mg of ethyl 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoate was dissolved in 0.2 ml of ethanol and 2.32 ml of an ethanol/water (10/1) solution of 2N potassium hydroxide was added thereto. The mixture was stirred at room temperature for 3 hours and further stirred for 1 hour at 55° C. 24 ml of water was added to the reaction solution, and the reaction solution was adjusted to pH 2 with 1N hydrochloric acid under cooling with ice. The solution was extracted three times with ethyl acetate, and the organic layer was washed with sequentially water and a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 375 mg of 3-[(4S,5S)-3-benzyloxycarbonyl-2,2-dimethyl-4-isobutyloxazolidin-5-yl]-2-isopropyl-2-propenoic acid as a colorless oily substance.

Provenance & Evidence