Dimethyl Sulfoxide → HCID 67778374, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-({5-[5-(cyclopropylmethoxy)-1,3-benzoxazol-2-yl]isoxazol-3-yl}oxy)-1-(fluoromethyl)ethyl methanesulfonate (97.3 mg), sodium azide (29.7 mg) and dimethyl sulfoxide (2 mL) was stirred at 100° C. for 4 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was mixed with triphenylphosphine (71.8 mg), THF (3 mL) and water (1 mL), and the obtained mixture was stirred at 90° C. for 2 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was mixed with acetic anhydride (1 mL), triethylamine (1 mL) and ethyl acetate (3 mL), and the obtained mixture was stirred at 60° C. overnight. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate). The obtained residue was separated by HPLC (C18, mobile phase: water/acetonitrile (containing 0.1% TFA)). A saturated aqueous sodium hydrogen carbonate solution was added to the obtained fraction, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound as white crystals (52.3 mg).

Provenance & Evidence