Water → methyl 4-[1-[4-[N'-(2,6-dichlorophenyl)ureido]-3-methoxyphenylacetyl]-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate

Participants

Reaction Steps

To a stirred solution of methyl 4-[5-(R)-phenyl-2-(S)-pirrolidinylmethoxy]benzoate (109 mg, 0.35 mmol), 4-[N′-(2,4-dichlorophenyl)ureido]-3-methoxyphenylacetic acid (129 mg, 0.35 mmol) and N,N-dimethylaminopyridine (42.8 mg, 0.35 mmol) in DMF (10 ml) was added EDC.HCl (73.4 mg, 0.39 mmol) at rt, and the resulting mixture was stirred for 6 h. The reaction mixture was poured into water and extracted with EtOAc. The organic layer was washed with brine, drying over anhydrous Na2SO4, then concentrated in vacuo. The residue was chromatographed on silica gel with hexane-EtOAc (1:4) as eluent to give methyl 4-[1-[4-[N′-(2,6-dichlorophenyl)ureido]-3-methoxyphenylacetyl]-5-(R)-phenyl-2-(S)-pyrrolidinylmethoxy]benzoate (208 mg, 90%) as a colorless amorphous solid. 1H-NMR (CDCl3) δ2.00-2.21 (m, 3 H), 2.33-2.39 (m, 1 H), 3.31 (s, 2 H), 3.69 (s, 3 H), 3.88 (s, 3 H), 4.34-4.45 (m, 2 H), 4.59 (brs, 1 H), 4.93 (t, J=6.8 Hz, 1 H), 6.47 (d, J=8.0 Hz, 1 H), 6.63 (s, 1 H), 6.68 (s, 1 H), 6.92-6.95 (m, 2 H), 7.12-7.41 (series of m, 9 H), 7.96-8.01 (m, 4 H); MS (FAB) m/z, 662 (M++H).

Provenance & Evidence