Triethylamine → HCID 9848030, compound

Participants

Reaction Steps

To a solution of this alcohol (300 mg, 0.86 mmol) in THF (5 ml) were added triethylamine (172 mg, 1.7 mmol) and 4-dimethylaminopyridine (10 mg, 0.09 mmol), then methanesulfonyl chloride (115 mg, 1.0 mmol) was dropped there into with ice-cooling and stirring, and the mixture was stirred for 40 minutes. After that, triethylamine (172 mg, 1.7 mmol) was further added thereto, then methanesulfonyl chloride (115 mg, 1.0 mmol) was dropped thereinto with ice-cooling and stirring, and the mixture was stirred for 20 minutes. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with water, an aqueous solution of sodium bicarbonate and a saturated sodium chloride solution successively and dried over anhydrous sodium sulfate, and the solvent was evaporated therefrom. The resulting residue was dissolved in DMF (7 ml), then 2-mercaptobenzooxazole (130 mg, 0.86 mmol), potassium carbonate (180 mg, 1.3 mmol) and 18-crown-6 (21 mg, 0.08 mmol) were added thereto, and the mixture was stirred at 80° C. for 1 hour. The reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous sodium sulfate and the solvent was evaporated therefrom. The residue was purified by a silica gel column chromatography (40 g of silica gel; developing solvent, hexane:acetone=5:1˜10:3) and the resulting crystals were recrystallized from acetone-hexane to provide 326 mg (yield 79%) of the desired compound as colorless needles.

Provenance & Evidence