Potassium Carbonate → Potassium 5-(4'-{[5-({1-[({[(5R)-5,6-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethoxy}-carbonyl)-2-butyl-4-chloro-1H-imidazol-1-yl]methyl}biphenyl-2-yl)tetrazol-1-ide

Participants

Reaction Conditions

Reaction Steps

Potassium carbonate (945 mg, 6.84 mmol) was added to a stirred solution of 1-[({[(5R)-5,6-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethyl 2-butyl-4-chloro-1-{[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate (250 mg, 0.34 mmol) in IPA (6.8 mL). The solution was stirred at 25° C. for 3 h. The reaction mixture was filtered and the filtrate was concentrated in vacuo. The residue was redissolved in DCM (6 mL). Heptane was added until the compound began to precipitate. The solution was concentrated in vacuo to give the title compound as a white solid. 1H NMR (500 MHz, CD3CN) δ 7.72-7.68 (m, 1H), 7.40-7.33 (m, 2H), 7.33-7.28 (m, 1H), 7.12 (d, J=8.5 Hz, 2H), 6.87 (d, J=8.0 Hz, 2H), 6.88-6.82 (m, 1H), 5.47 (s, 2H), 5.32 (ddd, J=13.0, 6.5, 2.5 Hz, 1H), 4.79 (dd, J=13.0, 2.5 Hz, 1H), 4.55 (dd, J=13.0, 6.5 Hz, 1H), 4.08 (td, J=6.5, 3.0 Hz, 2H), 1.71 (q, J=13.0, 7.7 Hz, 2H), 1.61 (hex, J=22.0, 14.5, 7.0 Hz, 4H), 1.50 (d, J=5.5 Hz, 3H) 1.49-1.37 (m, 2H), 1.35-1.26 (m, 2H), 0.85 (t, J=7.5 Hz, 3H); LCMS (M+H) found 731.1.

Provenance & Evidence