3-Amino-3-(4-methoxyphenyl)propanoic acid → HCID 21250922, compound

Participants

Reaction Steps

A stirred mixture of 2,3,4,5-tetrachlorophthalic acid anhydride (2.85 g, 10.0 mmol) and 3-amino-3-(4'-methoxyphenyl)propionic acid (1.95 g, 10.0 mmol) in 25 mL of acetic acid under nitrogen was heated to reflux for 4.5 hours. Solid formed as the reaction mixture cooled. The resulting slurry was filtered and the solid dried in vacuo (60° C., <2 mm) to afford 4.24 g (92%) of 3-(2,3,4,5-tetrachlorophthalimido)-3-(4'-methoxyphenyl)propionic acid as an off-white solid contaminated with ~ 1% acetic acid: mp 235.6°-238° C.; 1H NMR (DMSO-d6) δ 12.44 (br s, 1H, COOH), 7.36 (d, J=8.7 Hz, 2 H), 6.90 (d, 1 H, J=8.7 Hz), 5.64 (m, 1 H), 3.72 (s, 3 H), 3.35 (m, 2 H); 13C NMR (DMSO-d6) δ 171.5, 163.0, 158.8, 138.4, 129.9, 128.6, 128.2, 127.6, 113.8, 55.0, 50.2, 35.6. Anal. Calcd for C18H11NO5Cl4. Theory: C, 46.68; H, 2.39; N, 3.02. Found: C, 46.58; H, 2.31; N, 2.91.

Provenance & Evidence