Potassium Carbonate → Phenyl 5-(1-hydroxy-2-methylpropan-2-yl)isoxazol-3-ylcarbamate

Participants

Reaction Steps

To a stirred mixture of 2-(3-aminoisoxazol-5-yl)-2-methylpropan-1-ol from Step C (100 mg, 0.64 mmol) and potassium carbonate (166 mg, 1.20 mmol) in anhydrous tetrahydrofuran (15 mL) at rt, was added dropwise a solution of phenyl chloroformate (100 mg, 0.64 mmol) in tetrahydrofuran (6 mL). After stirring at rt for 15 h, the mixture was filtered and concentrated under reduced pressure. The residue was dissolved in dichloromethane (50 mL) and washed with water (50 mL), brine (50 mL), separated, and dried over MgSO4. The mixture was filtered and concentrated under reduced pressure. Crystallization from a mixture of ether and hexane afforded afforded phenyl 5-(1-hydroxy-2-methylpropan-2-yl)isoxazol-3-ylcarbamate as a colorless solid (120 mg, 68%). 1H NMR (300 MHz, CDCl3) δ 8.30 (brs, 1H), 7.42-7.43 (m, 2H), 7.26 (m, 1H), 7.16-7.21 (m, 2H), 6.65 (s, 1H), 3.67 (s, 2H), 1.98 (brs, 1H), 1.33 (s, 6H).

Provenance & Evidence