Hydrochloric Acid → HCID 9864811, compound

Participants

Reaction Steps

To a stirred solution of 3-amino-3-(3,4-diethoxyphenyl)propionic acid (1.03 g, 4.07 mmol) and sodium carbonate (0.453 g, 4.27 mmol) in a 1/1 mixture of 150 mL of acetonitrile/water (heated to 45° C. to dissolve) was added N-carbethoxyphthalimide (0.89 g, 4.07 mmol). The reaction mixture was stirred 1 hour, then partially concentrated in vacuo to remove the acetonitrile to afford a pale yellow solution. The stirred solution was acidified to pH 0-1 with 4 N hydrochloric acid to form a gum. The mixture was stirred overnight. The gum had not solidified and 1 mL of ether was added to mixture. The gum solidified on stirring and the slurry was filtered and the solid dried to afford 1.94 g (94%) of 3-(3,4-diethoxyphenyl)-3-phthalimidopropionic acid as a yellow solid: 1H NMR (DMSO-d6, 250 MHz) 12.41 (br s, 1H, COOH), 8.10-7.75 (m, 4H, Ar), 7.15-6.85 (m, 3H, Ar), 5.62 (overlapping dd, 1H), 4.20-3.90 (m, 4H, 2OCH2), 3.51 (dd, 1H, J=16.5, 9 Hz), 3.25 (dd, 1H, J=16.5, 7 Hz), 1.5-0.9 (m, 6H, 2 CH3) 13C NM (DMSO-d6) 1717, 167.6, 147.9, 147.8, 134.6, 131.3, 131.0, 123.1, 119.4, 113.2, 112.7, 63.8, 63.7, 50.0, 36.0, 14.6, 14.6; Anal. Calcd for C21H21NO6 : Theory C, 65.79; H, 5.52; N, 3.65. Found: C, 65.54; H, 5.55; N, 3.62.

Provenance & Evidence