Hydrochloric Acid → 4-[3-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl-N-methylamino]-1-propyl]benzoic acid

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Reaction Steps

To a stirred solution of ethyl 4-[3-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl-N-methylamino]-1-propyl]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) δ1.68-1.80 (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, 1 H), 6.87 (d, J=11.2 Hz, 1 H), 6.93 (t, J=7.3 Hz, 1 H), 7.15 (m, 2 H), 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+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.

Provenance & Evidence