反应详情

To a suspension of 2-methyl-N-(thietan-3-yl)-4-[(5S)-5-(3,4,5-trichlorophenyl)-5-(trifluoromethyl)-4H-isoxazol-3-yl]benzamide in dichloromethane (92 mL) was added m-CPBA (24.3 mmol, 5.58 g) portion wise at 0-5° C., and the reaction mixture was stirred for 10 min. A saturated Na2S2O3 solution was added, and the mixture was stirred for 10 min. The organic layer was washed with sat. NaHCO3 solution, water and brine, dried over MgSO4, filtered and evaporated. Purification over silica gel (eluent: CH2Cl2/EtOAc) yielded the title compound. LCMS (Method GR) 1.13 min, M+ 539/541; 1H NMR (400 MHz, CDCl3) 2.50 (s, 3H), 3.28 (m, 1H), 3.70 (d, 1H), 4.10-4.20 (m, 4H), 4.70 (m, 1H), 6.50 (d, 1H), 7.40-7.70 (1d+4s, 5H), 19F-NMR (CDCl3, 376 MHz): −79.43. Chiral HPLC Method Column: Daicel CHIRALPAK® IB, 3 μm, 0.46 cm×10 cm Mobile phase: Heptan/EtOH 80/20 Retention times of eluting isomers: 4.85 min (8.2%) 5.66 min (91.8%).

1. stirringthe mixture was stirred for 10 min
2. washThe organic layer was washed with sat. NaHCO3 solution, water and brine
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. customevaporated
6. customPurification over silica gel (eluent: CH2Cl2/EtOAc)