反应详情

To a stirred solution of ethyl 4-[3-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenyl acetyl-N-methylamino]-1propyl]benzoate (500 mg, 0.966 mmol) in THF (8 mL) was added 0.25 N NaOH (8 mL), and the mixture was heated under reflux overnight. The resulting solution was poured into ice-1 N HCl (100 mL) and the solid was collected with suction. The solid was dissolved in CHCl3 (100 mL) and dried over MgSO4. After removal of the solvent, the residue was chromatographed on silica gel with CHCl3-MeOH (10:1 to 5:1, v/v) to give 131 mg (28%) 4-[3-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl-N-methylamino]-1-propyl]benzoic acid 269 as a pale yellow amorphous solid. 1H-NMR (DMSO-d6) δ 1.68–1.80 (m, 2 H), 2.24 (s, 3 H), 2.57 (m, 2 H), 2.81 and 2.97 (s, each, total 3 H), 3.33 (m, 2 H), 3.57–3.61 (m, 2 H), 3.84 (s, 3 H), 6.71 (dd, J=29.8, 8.3 Hz, 1H), 6.87 (d, J=11.2 Hz, 1H), 6.93 (t, J=7.3 Hz, 1H), 7.15 (m, 2H), 7.28 (m, 2 H), 7.79 (d, J=8.3 Hz, 1 H), 7.84–7.87 (m, 2 H), 8.02 (d, J=8.3 Hz, 1 H), 8.49 (d, J=7.3 Hz, 1 H), 8.58 (d, J=4.9 Hz, 1 H); MS (FAB) m/z 490 (M++1); Anal. Calcd for C28H31N3O5.1/2H2O: C, 67.45; H, 6.47; N, 8.43. Found: C, 67.27; H, 6.51; N, 8.02.

1. temperaturethe mixture was heated
2. temperatureunder reflux overnight
3. customthe solid was collected with suction
4. dissolutionThe solid was dissolved in CHCl3 (100 mL)
5. dry with materialdried over MgSO4
6. customAfter removal of the solvent
7. customthe residue was chromatographed on silica gel with CHCl3-MeOH (10:1 to 5:1