pentafluorophenyl 3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetate → methyl (S)-3-nitro-4-[2-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenyl acetylamino]-1-propoxy]benzoate

Participants

Reaction Steps

A mixture of pentafluorophenyl 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetate (591 mg, 1.23 mmol), methyl (S)-3-nitro-4-(2-amino-1-propoxy)benzoate (313 mg, 1.23 mmol), and Et3 N (257 mL, 1.84 mmol) in DMF (5 mL) was stirred at room temp for 2 days. The mixture was diluted with EtOAc, washed with 0.5 N HCl, brine, dried over Na2SO4, and evaporated. The residue was purified by column chromatography on silica-gel with 5% MeOH in CHCl3 as eluent to give 310 mg (46%) methyl (S)-3-nitro-4-[2-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenyl acetylamino]-1-propoxy]benzoate as a gum. 1H-NMR (CDCl3) δ 1.28 (d, 3 H, J=6.8 Hz), 2.31 (s, 3 H), 3.49 (s, 2H), 3.71 (s, 3 H), 3.92 (s, 3 H), 4.14–4.16 (m, 2 H), 4.38–4.41 (m, 1 H), 5.88–5.90 (m, 1 H), 6.49 (s, 1 H), 6.70–6.71 (m, 1 H), 6.77–6.79 (m, 1 H), 7.05–7.30 (m, 4 H), 7.55–7.57 (m, 1 H), 8.02–8.06 (m, 2 H), 8.16–8.19 (m, 1 H), 8.51–8.52 (m, 1 H); MS (FAB) m/z 551 (M++1).

Provenance & Evidence