Oleic Acid → HCID 67807226, compound

Participants

Reaction Steps

A solution of 420 mg (1.08 mmol) of benzyl rac-α-[[(2-hydroxy-1,1-dimethylethyl)sulfonyl]methyl]hydrocinnamate, 610 mg (2.15 mmol) of oleic acid, 710 mg (1.88 mmol) of HBTU and 660 mg (5.38 mmol) of 4-dimethylaminopyridine in 10 ml of methylene chloride was stirred at room temperature for 15 hours. The reaction solution was subsequently poured into 70 ml of ice-cold 2N sodium carbonate solution and extracted three times with 150 ml of ethyl acetate each time. The organic extracts were washed with 70 ml of ammonium chloride solution, then combined, dried over magnesium sulphate and evaporated under reduced pressure. For purification, the crude product (1.25 g) was chromatographed on 50 g of silica gel with a 95:5 mixture of toluene and ethyl acetate as the eluent. There were obtained 580 mg of benzyl rac-α-[[[1,1-dimethyl-2-[[(Z)-9octadecenoyl]oxy]ethyl]sulfonyl]methyl]hydrocinnamate as a colourless oil, MS: 655 (M+H)+.

Provenance & Evidence