反应详情

To a stirred solution of 3-amino-3-(4-benzyloxy-3-methoxyphenyl)propionic acid (1.505 g, 5.00 mmol) and sodium carbonate (0.572 g, 5.40 mmol) in a mixture of 75 mL of water and 175 mL of acetonitrile (mixture was warmed gently to dissolve solid) was added N-carbethoxyphthalimide (1.096 g, 5.00 mmol). The mixture was stirred for 1 hour, then partially concentrated in vacuo to remove the acetonitrile. A small amount of solid formed which was removed by filtration. The pH of the solution was adjusted to 1 with 4N Hydrochloric acid, a gum formed. To the stirred mixture was added 1 mL of ether and the mixture was then stirred overnight. The resulting slurry was filtered and the solid dried to afford 1.63 g (75%) of 3-phthalimido-3-(4-benzyloxy-3-methoxyphenyl)-propionic acid as a white powder, 1H NMR (DMSO-d6) δ12.43 (br s, 1H, COOH), 8.0-7.8 (m, 4H, Ar), 7.60-7.25 (m, 5H), 7.15-6.85 (m, 3H, Ar), 5.25 (dd, 1H, J=9, 6.6 Hz), 5.05 (s, 2H, OCH2), 3.76 (s, 3H, OMe), 3.52 (dd, 1H, J=9, 16.5 Hz), 2.29 (dd, 1 H, J=6.6, 16.5 Hz); 13C NMR (DMSO-d6) δ171.7, 167.6, 148.9, 147.3, 137.0, 134.6, 131.7, 131.0, 128.3, 127.7, 127.6, 123.1, 119.1, 113.3, 111.3, 69.8, 55.5, 50.1, 36.0. Anal. Calcd for C25H21N1O6. Theory: C, 69.66; H, 4.91; N, 3.25. Found: C, 69.50; H, 4.85; N, 3.22.

1. temperaturewas warmed gently
2. dissolutionto dissolve solid)
3. concentrationpartially concentrated in vacuo
4. customto remove the acetonitrile
5. customA small amount of solid formed which
6. customwas removed by filtration
7. customa gum formed
8. stirringthe mixture was then stirred overnight
9. filtrationThe resulting slurry was filtered
10. customthe solid dried