Isopropanol → HCID 12051481, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (2S,3S)-3-[[1-(S)-[α-(R)-methoxybenzyl]-3-methylbutyl]carbamoyl]oxirane-2-carboxylic acid (105 mg, 0.327 mmol), 2-propanol (30 μl, 0.40 mmol.) and 4-dimethylaminopyridine (8 mg, 0.07 mmol.) in anhydrous dichloromethane (4 mL) was added 1,3-dicyclohexylcarbodiimide (75 mg, 0.36 mmol.) under chilling with ice. The resulting mixture was stirred at 5° C. for 30 minutes, and then stirred overnight at room temperature. The mixture was placed under reduced pressure to distill off the solvent. The residue was mixed with ethyl acetate and 10% citric acid, and the insoluble material was removed by filtration. The filtrate was successively washed with water, aqueous saturated sodium hydrogen carbonate solution, and aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by middle pressure silica gel column chromatography (n-hexane/ethyl acetate=3/1), to give the titled compound as a white crystalline product (70 mg, yield: 59%).

Provenance & Evidence