3-Nitrobenzenesulfonyl chloride → HCID 53668975, compound

Participants

Reaction Steps

3-Nitro-benzenesulfonyl chloride was reacted with glycine benzyl ester and the resulting (3-nitro-benzensulfonylamino)-acetic acid benzyl ester was reduced with tin chloride to afford (3-amino-benzenesulfonylamino)-acetic acid benzyl 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 benzyl ester was hydrolysed 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), 9.71 (1H, br s), 8.35 (1H, s), 7.96 (2H, m), 7.45 (2H, m), 3.57 (2H, s), 2.88 (2H, m), 2.60 (1H, m), 1.94-1.32 (27H, m). The acid was converted to the N-methyl-D-glucamine salt and lyophilised from water/dioxan. Found: C, 55.50; H, 7.88; N, 8.83%. C37H57N5O10.2.0 mols H2O requires: C, 55.55; H, 7.69; N, 8.75%.

Provenance & Evidence