Dimethyl Sulfoxide → HCID 68958974, compound

Participants

Reaction Conditions

Reaction Steps

To a stirring solution consisting of oxalyl chloride (5.0 mL) in dichloromethane (115 mL) at −78° C. is added dropwise a solution consisting of dimethyl sulfoxide (8.2 mL) in dichloromethane (25 mL) over ten minutes. The mixture is stirred at −78° C. for 40 minutes and a solution consisting of (±)-1-(1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropyl)-propan-1-ol (synthetic intermediate prepared in Example 47, 18.70 g) in dichloromethane (150 mL) is subsequently added dropwise over one hour. The mixture is stirred at −78° C. for an additional 30 minutes and excess triethylamine is subsequently added dropwise. The stirring mixture is allowed to warm gradually to room temperature overnight. The stirring mixture is treated with water. The layers are separated and the aqueous layer is extracted with a fresh portion of dichloromethane. The combined organic extracts are washed with brine solution, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography. Elution with hexanes-ethyl acetate (17:3 v/v) afforded the synthetic intermediate 1-(1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropyl)-propan-1-one (17.90 g.)

Provenance & Evidence