反应详情

Into a 50-mL round-bottom flask, was placed 4-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]piperazine-2,6-dione (200 mg, 0.36 mmol, 1.00 equiv), 1,1,1-trifluoro-3-iodopropane (163.5 mg, 0.73 mmol, 2.00 equiv), N,N-dimethylformamide (10 mL), potassium carbonate (100.7 mg, 0.73 mmol, 2.00 equiv). The resulting solution was stirred overnight at room temperature. The resulting solution was diluted with 60 mL of H2O. The resulting solution was extracted with 3×20 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 4×40 mL of brine. The mixture was dried over anhydrous sodium sulfate. The resulting mixture was concentrated under vacuum. The crude product (85 mg) was purified by Prep-HPLC. This resulted in 39.5 g (17%) of 4-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-1-(3,3,3-trifluoropropyl)piperazine-2,6-dione as a white solid. (ES, m/z): [M+CH3CN]+ 685.0; 1H NMR (300 MHz, CDCl3): δ 7.85 (s, 1H), 7.78 (s, 1H), 7.72 (s, 1H), 7.61 (d, J=8.7 Hz, 2H), 7.28-7.23 (m, 1H), 4.79 (s, 2H), 4.19-4.10 (m, 5H), 3.75 (d, J=17.4 Hz, 1H), 2.49-2.41 (m, 2H), 2.32 (s, 3H)

1. customInto a 50-mL round-bottom flask, was placed
2. extractionThe resulting solution was extracted with 3×20 mL of ethyl acetate
3. washThe resulting mixture was washed with 4×40 mL of brine
4. dry with materialThe mixture was dried over anhydrous sodium sulfate
5. concentrationThe resulting mixture was concentrated under vacuum
6. customThe crude product (85 mg) was purified by Prep-HPLC
7. customThis resulted in 39.5 g (17%) of 4-[(4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methylphenyl)carbonyl]-1-(3,3,3-trifluoropropyl)piperazine-2,6-dione as a white solid