5,6-Bis(nitrooxy)hexan-1-ol → 1-[({[5,6-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]-1-methylethyl 2-ethoxy-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate

Participants

Reaction Steps

6-Hydroxyhexane-1,2-diyl dinitrate (intermediate 1, 0.082 g, 0.36 mmol) and N,N-dimethylaminopyridine (0.029 g, 0.11 mmol) were added to a stirred dichloromethane (3.5 mL) solution of 1-methyl-1-{[(4-nitrophenoxy)carbonyl]oxy}ethyl 2-ethoxy-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-benzimidazole-7-carboxylate (intermediate 9, 0.220 g, 0.24 mmol). The solution was stirred at room temperature for 18 hours. Then it was washed with a 5% solution of sodium dihydrogenphosphate (2×10 mL) and brine (10 mL). The organic layer was dried over sodium sulfate, concentrated and purified by flash chromatography (Biotage SP1, 25+M column, TLC method n-hexane/EtOAc 6/4, Rf 0.4), affording the title compound as a white solid. 1H NMR (300 MHz, CDCl3) δ 8.04-8.01 (m, 1H), 7.63-7.61 (m, 2H), 7.46-7.18 (m, 12H), 6.98-6.90 (m, 8H), 6.91 (t, 1H), 6.81 (d, 3H), 6.68 (d, 2H), 5.62 (s, 2H), 5.25-5.23 (m, 1H), 4.72 (dd, 1H), 4.28-4.26 (m, 2H), 4.05 (t, 2H), 1.78-1.52 (m, 10H), 1.49-1.42 (m, 6H).

Provenance & Evidence