反应详情

A solution of 5,7-dichloro-3-(4-hydroxy-phenyl)-3-methyl-1H-quinoline-2,4-dione (0.45 g, 1.30 mmol) and triethylamine (0.18 mL) in dichloromethane (15 mL ) was added (S)-methyl benzylisocyanate (0.15 g, 1.56 mmol) at 0° C. The reaction mixture was stirred for 20 hours at room temperature, and then poured into ice water (100 mL). The reaction mixture was extracted with dichloromethane (100 mL×3), washed with brine (100 mL×2), dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by a flash column chromatography (n-hexane:EtOAc=7:1) to afford the unseparable diastereomeric 1:1 mixture (0.50 g, 80%) of the objective diastereomers: 1H NMR (500 MHz, DMSO-d6) δ 1.37 (d, J=7.0 Hz, 3H, CH3), 1.54 (s, 3H, CH3, one diastereomeric peaks), 1.64 (s, 3H, CH3, the other diastereomeric peaks), 4.65 (q, 1H, CH), 7.01-7.3 (m, 11H, ArH), 8.35 (br s, 1H, NH), 11.28 (br s, 1H, NH); m.p. 110-115° C. (diastereomeric 1:1 mixture); MS(EI) m/e 483 [M+−1], 335, 269, 120.

1. extractionThe reaction mixture was extracted with dichloromethane (100 mL×3)
2. washwashed with brine (100 mL×2)
3. dry with materialdried over anhydrous MgSO4
4. concentrationconcentrated in vacuo
5. customThe residue was purified by a flash column chromatography (n-hexane:EtOAc=7:1)