反应详情

(S)-methyl 2-(3-(4-(3-(2-fluorophenyl)ureido)phenyl)isoxazole-5-carboxamido)-3-hydroxypropanoate (compound of Example 275, 500 mg, 1.13 mmol) was taken in DCM and mesyl chloride (0.13 ml, 1.69 mmol) and Et3N (0.24, 1.69 mmol) were added and the reaction mixture was stirred at RT for half an hour. Water was added to quench the reaction and the organic layer was extracted with DCM. Organic layer was dried over Na2SO4 and concentrated under vacuum. Crude compound was purified by precipitation using DCM and petroleum ether to yield 140 mg (30%) of the required compound as white solid. MS: ES (+) m/z 425(M+1); 1HNMR (DMSO-d6, 300 MHz) δ: 10.241 (s, 1H), 8.367 (s, 1H), 8.656 (d, 1H), 8.180 (t, 1H), 7.907 (d, 2H), 7.769 (s, 1H), 7.645 (d, 2H), 7.290 (m, 1H), 7.189 (t, 1H), 7.067 (m, 1H), 6.046 (s, 1H), 5.918 (s, 1H), 3.782 (s, 3H).

1. customto quench
2. customthe reaction
3. extractionthe organic layer was extracted with DCM
4. dry with materialOrganic layer was dried over Na2SO4
5. concentrationconcentrated under vacuum
6. customCrude compound was purified by precipitation