Cyclohexanecarboxaldehyde → HCID 57257056, compound

Participants

Reaction Steps

5-(Adamantan-1-yloxymethyl)-2-cyclohept-4-enyl-1H-imidazole-4-carboxylic acid benzyl ester was prepared according to the procedure of Example 216, steps a, b, c, d with the modification that cyclohept-4-enecarboxaldehyde (D. F. Murray et al. J. Org. Chem. 1986, 51, 1) 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-cyclohept4-enyl-1H-imidazole4-carboxylic acid was reacted with (3-amino-phenyl)-acetic acid benzyl ester according to the procedure of Example 20, step d to afford (3-{[5-(adamantan-1-yloxymethyl)-2-cyclohept-4-enyl-1H-imidazole-4-carbonyl]-amino}-phenyl)-acetic 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) 12.25 (2H, br m), 9.45 (1H, br s), 7.62 (2H, m), 7.24 (1H, t), 6.94 (1H, d), 5.82 (2H, br s), 4.78 (2H, s), 3.53 (2H, s), 3.03 (1H, m), 2.30 (2H, m), 2.13 (5H, m), 1.94 (2H, m), 1.76-1.58 (14H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 60.40; H, 8.07; N, 7.72%. C37H54N4O9.2.1 mols H2O requires: C, 60.38; H, 7.96; N, 7.61%.

Provenance & Evidence