3-Nitrobenzoic acid → HCID 11769697, compound

Participants

Reaction Steps

3-Nitro-benzoic acid was reacted with glycine methyl hydrochloride and the resulting (3-nitro-benzoylamino)-acetic acid methyl ester was hydrogenated to afford (3-amino-benzoylamino)-acetic acid methyl ester. This 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 methyl ester was hydrolysed using the same procedure as in Example 36, step d to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 10.54 (1H, br s), 8.80 (1H, t), 8.25 (1H, s), 7.91 (1H, d), 7.61 (1H, d), 7.45 (1H, d), 3.92 (2H, m), 2.93 (3H, m), 1.98-1.33 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 57.22; H, 8.30; N, 8.81%. C38H57N5O9.4.0 mols H2O requires: C, 57.06; H, 8.19; N, 8.75%.

Provenance & Evidence