tert-Butanol → HCID 86655408, compound

Participants

Reaction Steps

To a solution of 3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzooxazol-6-yl}oxy)benzoic acid (8.6 g) in tetrahydrofuran (100 mL) and 2-methylpropan-2-ol (50 mL) were added N-ethyl-N-isopropylpropane-2-amine (20 L, 115 mmol) and diphenylphosphoryl azide (22 mL, 102 mmol), and the mixture was heated under reflux for 6 hr. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was dissolved in ethyl acetate (250 mL), and the mixture was washed with saturated aqueous sodium hydrogencarbonate solution (100 mL×2) and saturated brine (100 mL), successively, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=2/98→80/20) to give the objective tert-butyl [3-({2-[(cyclopropylcarbonyl)amino]-1,3-benzooxazol-6-yl}oxy)phenyl]carbamate as a brown amorphous substance (3.25 g). The obtained compound was used in the next operation without further purification.

Provenance & Evidence