1,2-Dichloroethane → Benzoic Acid

Participants

Reaction Steps

To a stirred mixture of ethyl 4-(2-allylaminoethoxy)-3-methoxy benzoate (578 mg, 2.1 mmol), 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylaceticacid (650 mg, 2.1 mmol), HOBt (420 mg, 3.11 mmol), and DMAP (catalytic amount) in DMF (4 mL) was added EDC (596 mg, 3.11 mmol) at room temp. The resulting mixture was stirred for a further 18 hr at room temp. The mixture was poured into 1N HCl and extracted with EtOAc. The extract was washed with brine, dried over Na2SO4, and evaporated in vacuo. The residue was chromatographed on silica-gel with CHCl3:EtOAc (95:5 to 1:1, v/v) as eluent to give 1 g (84%) 3-methoxy-4-[[2-3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]allylamino]ethoxy]benzoic acid as a pale-yellow gum. 1H-NMR (CDCl3, 400 MHz) δ1.39 (t, 3H, J=7.3 Hz), 2.29 (s, 3H), 3.58 and 3.63 (s, total 3H), 3.70-3.77 (m, 2H), 3.83 and 3.87 (s, 3H), 4.054.13 (m, 2H), 4.25 (m, 1H), 4.36 (q, 1H, J=7.0 Hz), 5.04-5.22 (m, 2H), 5.73 (m, 1H), 6.32 and 6.47 (s, 1H), 6.69-6.85 (m, 2H, 7.12 (m, 2H), 7.23 (m, 2H), 7.50-7.65 (m, 2H), 8.05 (d, 1H, J=7.8 Hz); MS (FAB) m/z 576(M+H)30.

Provenance & Evidence