Acetone → 3-(2-(N-tert-Butoxycarbonylamino)ethoxy)-4-(1-hydroxyisopropyl)-5-phenylisoxazole

Temperature

-70 °C

3-(2-(N-tert-Butoxycarbonylamino)ethoxy)-5-phenylisoxazole (0.8 g) was dissolved in tetrahydrofuran (16 ml), butyllithium (1.6M hexane solution, 3.7 ml) was added dropwise thereto at -70° C. under a nitrogen atmosphere, and the resulting mixture was stirred at the same temperature for 10 minutes. After acetone (0.3 ml) was added dropwise to the reaction mixture and the mixture was stirred for 10 minutes, the temperature of the mixture was raised to 0° C. The reaction mixture was poured into ice-cold water and the pH of the mixture was adjusted to a value of 6 with an aqueous potassium dihydrogenphosphate solution. The mixture was extracted with ethyl acetate and the organic layer was washed with a saturated aqueous NaCl solution, followed by evaporation of the solvent under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1) to obtain the title compound (0.42 g, 44%) as a colorless oil.

1. stirringthe mixture was stirred for 10 minutes
2. temperaturethe temperature of the mixture was raised to 0° C
3. additionThe reaction mixture was poured into ice-cold water
4. extractionThe mixture was extracted with ethyl acetate
5. washthe organic layer was washed with a saturated aqueous NaCl solution
6. customfollowed by evaporation of the solvent under reduced pressure
7. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1)

ORD record

ord-4f3220a82a074060bd7e8148c16da030

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06005116