Sodium Carbonate → HCID 3121010, compound

Participants

Reaction Steps

To a stirred mixture of 3-amino-3-(4-methoxyphenyl)propionic acid (1.95 g, 10.0 mmol) and sodium carbonate (1.11 g, 10.5 mmol) in 200 mL of acetonitrile-water 1:1 is added N-carboethoxyphthalimide (2.26 g, 10.0 mmol). After 1 hour, the reaction slurry is filtered. The filtrate is concentrated to remove the acetonitrile and the pH adjusted to 1-2 with 4N hydrochloric acid and stirred over night. The resulting slurry is filtered and the solid washed with water. The solid is dried in vacuo (60 C, <1 mm) to afford 2.82 g (87%) of 3-phthalimido-3-(4-methoxyphenyl)propionic acid as a white powder: mp 160°-164° C.; 1H NMR (DMSO-6, 250 MHz) δ12.5 (br s, 1H), 7.95-7.80 (m, 4H), 7.36 (d, 2H, J=8.7), 6.92 (d, 2H, J=8.4 Hz), 5.18-5.10 (m, 1H), 3.70-3.15 (m, 2H); 13C NMR (DMSO-d6) δ171.7, 167.6, 158.6, 134.6, 131.0, 130.8, 128.3, 123.1, 113.9, 55.0, 49.6, 35.9. Anal. Calculated for C18H15 NO5. Theoretical: C, 66.46; H, 4.63; N, 4.31. Found: C, 66.25; H, 4.65; N, 4.28.

Provenance & Evidence