反应详情

温度

70 °C

To a stirred solution of benzylcis-4-[[1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenyl acetyl]-2-pyrrolidinyl]methylamino]cyclohexanecarboxylate (1.5 g, 2.45 mmol) in THF (10.0 ml) and MeOH (5.0 ml) was added 1N NaOH (3.68 ml, 3.68 mmol). The mixture was stirred at 70° C. for 18 hr. The mixture was concentrated in vacuo, water was added thereto, and neutralized with 1N HCl. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with MeOH—CH2Cl2 (1:5, v/v) as eluent to give cis-4-[[1-[3-methoxy-4-[N′-(2-methyl phenyl)ureido]phenylacetyl]-2-pyrrolidinyl]methylamino]cyclohexanecarboxylic acid 171 (940 mg, 73%) as an amorphous solid. MW 522.64 IR (KBr) 3283, 2945, 2860, 1534, 1453, 1415 cm−1; 1H-NMR (DMSO-d6) δ1.38-2.00 (m, 12H), 2.45 (s, 3H), 2.30-3.95 (m, 4H), 3.22-3.75 (m, 2H), 3.58 (s, 2H), 3.86 (s, 3H), 4.12 (m, 1H), 6.73-7.16 (m, 5H), 7.77-7.79 (m, 1H), 7.98-8.02 (m, 1H), 8.51-8.52 (m, 1H), 8.57-8.59 (m, 1H); MS (FAB) m/z 523 (M++1); Anal. Calcd. for C29H38N4O5.0.5NaCl.2.2H2O: C, 58.89; H, 7.23; N, 9.47. Found: C, 59.21; H, 7.11; N, 9.11.

1. concentrationThe mixture was concentrated in vacuo, water
2. additionwas added
3. concentrationThe mixture was concentrated in vacuo
4. customThe residue was purified by column chromatography on silica gel with MeOH—CH2Cl2 (1:5