Cyclohexanecarboxaldehyde → HCID 69686100, compound

Participants

Reaction Steps

5-(Adamantan-1-yloxymethyl)-2-bicyclo[2.2.2]oct-2-en-1-yl-1H-imidazole-4-carboxylic acid benzyl ester was prepared according to the procedure of Example 216, steps a, b, c and d with the modification that bicyclo[2.2.2]oct-2-en-1-yl-carbaldehyde (prepared by reduction and then pyridinium chlorochromate oxidation of bicyclo[2.2.2]oct-2-en-1-yl-carboxylic acid ethyl ester (C. A. Grob, M. Ohta, E. Renk and A. Weiss, Helv. Chim. Acta 1958, 41, 1191)) was used in step d instead of cyclohexanecarboxaldehyde. The benzyl ester was hydrolysed according to the procedure of Example 211, step b and the resulting 5-(adamantan-1-yloxymethyl)-2-bicyclo[2.2.2]oct-2-en-1-yl-1H-imidazole4-carboxylic acid was reacted with 3-amino-benzoic acid benzyl ester according to the procedure of Example 177, step a to afford 3-{[5-(adamantan-1-yloxymethyl)-2-bicyclo[2.2.2]oct-2-en-1-yl-1H-imidazole4-carbonyl]-amino}-benzoic acid benzyl ester. The benzyl ester was hydrolysed according to the procedure of Example 211, step b to afford the title compound. 1H NMR (300 MHz, d6-DMSO) 12.35 (1H, br s), 9.69 (1H, s), 8.44 (1H, br s), 7.95 (1H, d), 7.62 (1H, d), 7.41 (1H, t), 6.73 (1H, d), 6.38 (1H, dd), 4.81 (2H, s), 2.63 (1H, br s), 2.11 (3H, br s), 1.97 (2H, td), 1.76 (6H, s), 1.67-1.53 (8H, m), 1.44 (2H, t), 1.30 (2H, t). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 56.61; H, 7.99; N, 7.35%. C37H52N4O9.5.0 mols H2O requires: C, 56.47; H, 7.94; N, 7.12%.

Provenance & Evidence