반응 #47349
ord-deeedffdbfe042ada35bfd687c5687e6
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반응물
시약
반응 조건
후처리
- 1세척was washed with a saturated aqueous sodium bicarbonate solution (1×100 mL)
- 2건조a saturated aqueous sodium chloride solution (1×100 mL), dried over sodium sulfate
- 3여과filtered
- 4농축concentrated in vacuo
- 5기타Purification by Analogix flash chromatography (40 g, 1-10% methanol/dichloromethane gradient)
실험 절차
A solution of (S)-2-[4-(4-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid [1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl-methyl)-1H-pyrazol-3-yl]-amide (0.38 g, 0.76 mmol) in methanol (7.66 mL) at 25° C. was treated with p-toluenesulfonic acid monohydrate (22 mg, 0.11 mmol). The reaction was stirred at 25° C. overnight. At this time, the reaction diluted with ethyl acetate (75 mL) and was washed with a saturated aqueous sodium bicarbonate solution (1×100 mL) and a saturated aqueous sodium chloride solution (1×100 mL), dried over sodium sulfate, filtered and concentrated in vacuo. Purification by Analogix flash chromatography (40 g, 1-10% methanol/dichloromethane gradient) afforded (S)-2-[4-(4-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-4-methyl-pentanoic acid [1-((R)-2,3-dihydroxy-propyl)-1H-pyrazol-3-yl]-amide (0.30 g, 86%) as a white solid: HR-ES-MS m/z calculated for C23H30N4O6 [M+H]+ 459.2238, observed 459.2237. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.90 (d, J=6.4 Hz, 3H), 0.93 (d, J=6.4 Hz, 3H), 1.36-1.64 (m, 2H), 1.66-1.81 (m, 1H), 3.20-3.32 (m, 2H), 3.77 (s, 4H), 3.86 (dd, J=13.3, 7.5 Hz, 1H), 4.04-4.11 (m, 1H), 4.14 (d, J=18.1 Hz, 1H), 4.53 (d, J=18.1 Hz, 1H), 4.71 (t, J=5.6 Hz, 1H), 4.75 (s, 1H), 4.87 (dd, J=10.6, 4.8 Hz, 1H), 4.93 (d, J=5.1 Hz, 1H), 6.40 (d, J=2.1 Hz, 1H), 7.00 (d, J=9.1 Hz, 2H), 7.23 (d, J=9.1 Hz, 2H), 7.53 (d, J=2.1 Hz, 1H), 10.74 (s, 1H).