Cesium carbonate → 1-[({[(4R,5R)-3-methyl-4,5-bis(nitrooxy)hexyl]oxy}carbonyl)oxy]ethyl 2-butyl-4-chloro-1-{[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylate

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Reaction Steps

(4R,5R))-3-methyl-4,5-bis(nitrooxy)hexyl 1-chloroethyl carbonate (1.01 g, 3.26 mmol) was added to a stirred solution of 2-butyl-4-chloro-1-{[2′-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylic acid (Intermediate 3, 3.32 g, 4.88 mmol) and Cs2CO3 (2.40 g, 7.33 mmol) in DMF (18 mL). The solution was stirred at room temperature overnight. The mixture was diluted with a solution of NaH2PO4 5% (40 mL) and extracted with EtOAc (3×25 mL). The organic layer was washed with water (4×20 mL) and brine. The residue was purified by flash chromatography (Biotage SP1, SNAP 100 g column, TLC method: n-Hexane/EtOAc 7:3, RE 0.45) affording the title compound that was used in the next step without any further characterization.

Provenance & Evidence