(2R,3R)-6-hydroxy-4-methylhexane-2,3-diyl dinitrate → 1-[({[(4R,5R)-3-Methyl-4,5-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

(2R,3R)-6-hydroxy-4-methylhexane-2,3-diyl dinitrate (Intermediate 2, 0.78 g, 3.26 mmol) was added to a stirred 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 4, 1.96 g, 2.17 mmol) in CH2Cl2 (20 mL). The solution was stirred at room temperature overnight. The solution was diluted with CH2Cl2 (20 mL) washed with a solution of NaH2PO4 5% (2×20 mL) and brine. The organic layers were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by flash chromatography (Biotage SP1, SNAP 100 g column, TLC method, n-Hexane/EtOAc 6:4, Rf:0.45) affording the title compound that was used without any further purification.

Provenance & Evidence