Triethylamine → HCID 22272819, compound

Participants

Reaction Steps

To a solution of the alcohol (150 mg, 0.38 mmol) in THF (3 ml) were added triethylamine (50 mg, 0.50 mmol) and 4-dimethylaminopyridine (5 mg, 0.04 mmol), then methanesulfonyl chloride (53 mg, 0.46 mmol) was dropped thereinto with ice cooling and stirring, the mixture was stirred for 30 minutes. After the reaction, the reaction solution was diluted with water and extracted with ethyl acetate. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate and the solvent was evaporated. The resulting residue was dissolved in DMF (5 ml), then 5-chloro-7-isopropyl-2-mercapto-4-methylbenzoxazole (93 mg, 0.38 mmol), potassium carbonate (64 mg, 0.46 mmol) and 18-crown-6 (10 mg, 0.04 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, dried over anhydrous sodium sulfate and the solvent was evaporated. The resulting residue was purified by a silica gel column chromatography (developing solvent, chloroform:methanol=50:1) and the resulting crystals were recrystallized from ethyl acetate-hexane to provide 91 mg (yield 39%) of the desired compound as colorless powdery crystals.

Provenance & Evidence