Triethylamine → methyl (S)-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetylamino]-1-propoxy]benzoate

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Reaction Steps

A mixture of pentafluorophenyl 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetate (505 mg, 1.05 mmol), methyl (S)-4-(2-amino-1-propoxy)benzoate (220 mg, 1.05 mmol), and Et3N (0.220 mL, 1.58 mmol) in DMF (8 mL) was stirred at room temp for 3 hr. The mixture was diluted with EtOAc, washed with 0.5 N HCl, brine and dried over Na2SO4. After removal of the solvent, the residue was recrystallized from MeOH—CHCl3-n-hexane to give 290 mg (55%) methyl (S)-4-[2-[3-methoxy-4-[N′-(2-methylphenyl) ureido]phenylacetylamino]-1-propoxy]benzoate as a white crystalline powder. 1H-NMR (DMSO-d6) δ 1.18 (d, 3 H, J=6.8 Hz), 2.24 (s, 3 H), 3.36 (s, 2H), 3.80 (s, 3H), 3.82 (s, 3H), 3.93–4.03 (m, 2H), 4.09–4.14 (m, 1H), 6.75–8.57 (series of m, total 13 H).

Provenance & Evidence