Chloroform → HCID 178468440, compound

Participants

Reaction Steps

A mixture of ethyl 2-ethyl-3-[2'-(1-trityl-1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (1.51 g), acetic anhydride (0.44 g), sodium hydrogen carbonate (1.09 g), chloroform (18 ml) and water (18 ml) is stirred overnight at room temperature. The aqueous layer is extracted with chloroform, and the combined organic layer is washed with aqueous citric acid solution and brine, dried, and evaporated. To the residue (1.46 g) is added fumaric acid (1.2 g) and ethanol (20 ml), and the mixture is refluxed for four hours, then evaporated. The residue is treated with a saturated sodium hydrogen carbonate solution and then extracted with chloroform. The organic layer is dried and evaporated. Purification by silica gel column chromatography (solvent; chloroform/methanol) gives ethyl 2-ethyl-5-acetyl-3-[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl-4,5,6,7-tetrahydroimidazo[4,5-c]pyridine-4-carboxylate (0.76 g) as a white foam.

Provenance & Evidence