1,2-Dichloroethane → methyl 4-[[1-[4-[N'-(2-fluorophenyl)ureido]-3-methoxyphenylacetyl]methylamino]-2-methyl-2-propoxy]benzoate

Participants

Reaction Steps

To a stirred mixture of methyl 4-(1-methylamino-2-methyl-2-propoxy)benzoate (200 mg, 0.84 mmol), 4-[N′-(2-fluorophenyl)ureido]-3-methoxyphenylacetic acid (268 mg, 0.84 mmol), 4-DMAP (125 mg, 1.0 mmol) in DMF (5 mL) was added EDC (220 mg, 1.14 mmol) at ambient temp. The resulting mixture was stirred for a further 10 hr at ambient temp. The mixture was poured into water, and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and evaporated. The residual gum was triturated with CH2Cl2 and Et2O to give 200 mg (44.1%) methyl 4-[[1-[4-[N′-(2-fluorophenyl)ureido]-3-methoxyphenylacetyl]methylamino]-2-methyl-2-propoxy]benzoate as a crystalline material. 1H-NMR (CDCl3) δ1.36 and 1.31 (each s, 6H), 3.24-3.88 (series of s, 13 H), 6.65-8.20 (series of m, 14H).

Provenance & Evidence