3-(4-Aminophenyl)propionic acid → HCID 18405655, compound

Participants

Reaction Steps

3-(4-Amino-phenyl)-propionic acid acid benzyl ester (prepared in two steps from 4-nitrocinnamic acid) was reacted with 5-(2-adamantan-1-yl-ethyl)-2-cyclohexyl-1H-imidazole-4-carboxylic acid (Example 252) according to the procedure of Example 20, step d. The benzyl ester was hydrogenolysed using the same procedure as in Example 1, step e to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 12.00 (1H, br s), 9.28 (1H, br s), 7.63 (1H, d), 7.14 (1H, d), 2.86 (2H, m), 2.76 (2H, t), 2.64 (1H, m), 2.62 (2H, m), 2.49 (2H, m), 1.93-1.30 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.77; H, 8.69; N, 7.49%; C38H58N4O8.3.0 H2O requires: C, 60.62; H, 8.57; N, 7.44%.

Provenance & Evidence