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

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).

1. filtrationthe mixture was filtered
2. concentrationconcentrated under reduced pressure
3. dissolutionThe residue was dissolved in dichloromethane (50 mL)
4. washwashed with water (50 mL), brine (50 mL)
5. customseparated
6. dry with materialdried over MgSO4
7. filtrationThe mixture was filtered
8. concentrationconcentrated under reduced pressure
9. customCrystallization
10. additionfrom a mixture of ether and hexane
11. customafforded

ORD record

ord-112afd07265a4a498fb85ee7aa74d450

Source dataset

uspto-grants-2013_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08551963B2