反应详情

Into a 50 mL round-bottom flask was placed methyl 3-((3-((2-((2-phenylpyrimidin-5-yl)carbamoyl)-4-(piperidin-1-yl)phenyl)carbamoyl)-benzyl)thio)propanoate (crude product of 1459-084), and a solution of lithium hydroxide (387 mg, 9.21 mmol, 24.98 equiv) in water (2 mL). The resulting solution was stirred overnight at room temperature. The reaction progress was monitored by LCMS. The resulting solution was diluted with 20 mL of water and adjusted to pH 4-5 with hydrochloric acid (2 N). The resulting solution was extracted with 4×30 mL of ethyl acetate and the organic layers combined, washed with 1×50 mL of brine, dried over anhydrous sodium sulfate, and concentrated under vacuum. The resulting mixture was washed with 3×5 mL of ethyl ether. This resulted in 120 mg (55%) of product as a yellow solid. 1H-NMR (300 MHz, DMSO, ppm): δ 12.21 (s, 1H), 10.86-10.97 (d, 2H), 9.21 (s, 2H), 8.36-8.38 (m, 2H), 8.11 (m, 1H), 7.75-7.88 (m, 2H), 7.39-7.52 (m, 6H), 7.24 (m, 1H), 3.84 (s, 21-1), 3.23-3.33 (s, 4H), 2.56-2.61 (m, 4H), 1.58-1.67 (d, 6H). MS (ES, m/z): 596 [M+H]+.

1. customInto a 50 mL round-bottom flask was placed
2. extractionThe resulting solution was extracted with 4×30 mL of ethyl acetate
3. washwashed with 1×50 mL of brine
4. dry with materialdried over anhydrous sodium sulfate
5. concentrationconcentrated under vacuum
6. washThe resulting mixture was washed with 3×5 mL of ethyl ether