Dimethylformamide → (S)-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoic acid

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Reaction Steps

A mixture of pentafluorophenyl 4-[N′-(2-methylphenyl)ureido]phenylacetate (560 mg, 1.24 mmol), methyl (S)-4-(2-amino-1-propoxy)benzoate (260 mg, 1.24 mmol), Et3N (0.260 mL, 1.87 mmol) in DMF (8 mL) was stirred at room temp for 3 hr. The mixture was diluted with EtOAc and the solution was washed with 0.5 N HCl, brine, and dried over Na2SO4. After removal of the solvent, the residue was purified by recrystallization from MeOH—CHCl3-n-hexane to give 210 mg (36%) (S)-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoic acid as a white crystalline powder. 1H-NMR (DMSO-d6) δ1.17 (d, 3 H, J=6.8 Hz), 2.24 (s, 3 H), 3.32 (s, 2 H), 3.81 (s, 3 H), 3.92-4.03 (m, 2 H), 4.08-4.15 (m, 1 H), 6.92-6.95 (m, 1 H), 7.04-7.06 (m, 2 H), 7.12-7.18 (m, 4 H), 7.35-7.39 (m, 2 H), 7.83-7.85 (m, 1 H), 7.89-7.92 (m, 3 H), 8.12-8.14 (m, 1 H), 8.97 (s, 1 H).

Provenance & Evidence