Diisopropylethylamine → HCID 53630508, compound

Participants

Reaction Steps

Under argon gas stream, to 10 ml of an anhydrous dimethylsulfoxide-dichloromethane (1:1) solution containing 1.38 g (8.6 mmol) of sulfur trioxide pyridine complex salt were successively added dropwise at 0° C. 1.47 ml (8.6 mmol) of diisopropylethylamine, and then, 5 ml of an anhydrous dimethylsulfoxide solution containing 350 mg (0.7 mmol) of (2S)-N-[(2S,3S)-2-hydroxy-1-[N-[(1S,2S)-2-hydroxycyclohexane-1-yl]amino]-1-oxo-3-heptyl]-1-(phenylmethoxycarbonyl)pyrrolidine-2-carboxamide, and the resulting mixture was stirred at the same temperature for 5 hours. After completion of the reaction, to the reaction mixture was added 25 ml of ice-water, and the resulting mixture was extracted with 30 ml of ethyl acetate three times. The organic layers were combined, washed with 100 ml of a 10%-aqueous citric acid solution, 100 ml of a saturated aqueous sodium hydrogen carbonate solution, and then, 100 ml of a saturated NaCl solution, dried over anhydrous sodium sulfate, and then, concentrated under reduced pressure. The residue was purified by neutral silica gel column chromatography to obtain 300 mg (Yield: 86.1%) of the title compound.

Provenance & Evidence