反应详情

A mixture of 3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetic acid (89 mg, 0.283 mmol), methyl-2-[(2S,4S)-4-(2-naphthyloxy)-2-pyrrolidinyl]methoxypyridine-5-carboxylate (107 mg, 0.78 mmol), EDC.HCl (81 mg, 0.425 mmol) and DMAP (52 mg, 0.425 mmol) in DMF (3 ml) was stirred at room temperature for 18 h. The mixture was poured into ice water and extracted with EtOAc. The combined extracts were washed with ice water and brine. After dried over Na2SO4, the extracts were concentrated in vacuo. The residue was purified on TLC [CHCl3/MeOH (10/1)], to give 2-[(2S,4S)-1-[3-methoxy-4-[N′-(2-methylphenyl)ureido]phenylacetyl]-4-(2-naphthyloxy)-2-pyrrolidinyl]methoxy-5-pyridinecarboxylic acid methyl ester (193 mg, 100%) as a colorless amorphous. 1H-NMR (CDCl3) δ2.27 (d, J=3.2 Hz, 3H), 2.30 (m, 1H), 2.49 (dd, J=14.2, 2.0 Hz, 1H), 3.60 (d, J=3.9 Hz, 1H), 3.67 (d, J=5.9 Hz, 3H), 3.81 (s, 1H), 3.85 (s, 1H), 3.88 and 3.91 (s, 3H, amide isomers), 3.95 (m, 1H), 4.02-5.09 (m, 4H), 6.67 (d, J=8.8 Hz, 1H), 6.73-7.13 (m, 3H), 7.20-7.45 (m, 7H), 7.53 (t, J=7.8 Hz, 1H), 7.67-7.77 (m, 3H), 8.02-8.84 (m, 3H).

1. extractionextracted with EtOAc
2. washThe combined extracts were washed with ice water and brine
3. dry with materialAfter dried over Na2SO4
4. concentrationthe extracts were concentrated in vacuo
5. customThe residue was purified on TLC [CHCl3/MeOH (10/1)]