Sodium Hydroxide → HCID 178491570, compound

Participants

Reaction Conditions

Reaction Steps

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 1 N 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 1 N HCl. The mixture was concentrated in vacuo. The residue was purified by column chromatography on silica gel with MeOH—CH2C2 (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−; 1H-NMR (DMSO-d6) δ 1.38–2.00 (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.

Provenance & Evidence