Benzyl chloroformate → HCID 71542557, compound

Participants

Reaction Steps

(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (160 mg, 0.381 mmol) was dissolved in DCM (20 ml), and DMAP (0.056 g, 0.539 mmol) was added followed by benzyl chloroformate (0.077 ml, 0.539 mmol). The reaction mixture was stirred at RT for 6 hours. Additional benzyl chloroformate (0.077 ml, 0.539 mmol) was added, and stirring was continued at RT overnight. The reaction mixture was diluted with DCM and washed with aqueous saturated NH4Cl solution (20 mL). The organic layer was dried over sodium sulfate and evaporated to dryness. The crude was purified by chromatography on silica gel cartridge (DCM:ethyl acetate=8:2) to give 0.120 g of desired compound. A further purification by trituration with ethanol (10 mL) was required to afford (S)-4-(2-(benzyloxycarbonyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)ethyl)-3,5-dichloropyridine 1-oxide as a white amorphous solid (0.101 g, 0.182 mmol, 47.9% yield, MS/ESI+554.01 [MH]+, [αD]=−6.9, c=0.68, DCM).

Provenance & Evidence