1,2-Dichloroethane → methyl (S)-4-[1-[3-methoxy-4-[N'-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]benzoate

Participants

Reaction Steps

A mixture of 3-methoxy4-[N′-(2-methylphenyl)ureido]phenylacetic acid (428 mg, 1.36 mmol), methyl (S)-4-(2-pyrrolidinylmethoxy)benzoate (330 mg, 1.40 mmol), EDC (312 mg, 1.63 mg), HOBt (220 mg, 1.63 mmol), and a catalytic amount of DMAP in DMF (15 mL) was stirred for 6 hr. The resulting mixture was diluted with EtOAc, washed with 0.5 N HCl, sat. NaHCO3, brine, and dried over MgSO4. The solvent was evaporated off in vacuo to give an oily residue, which was purified by column chromatography on silica-gel with CHCl3-MeOH (50:1, v/v) as eluent to give 540 mg (75%) methyl (S)-4-[1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-2-pyrrolidinylmethoxy]benzoate as an oil. 1H-NMR (CDCl3) δ 1.81–2.12 (m, 4 H) 2.88 (bs, 3 H), 3.48–3.61 (m, total 7 H), 3.88 (s, 3 H), 4.10–4.21 (m, 2 H), 4.42–4.46 (m, 1 H), 6.75–8.08 (series of m, total 13 H).

Provenance & Evidence