Citric Acid → HCID 178440168, compound

Participants

Reaction Steps

5-Cyano-2-propyl-4-(1H-pyrrol-1-yl)-1-[(2'-(1H-tetrazol-5-yl)biphen-4-yl)methyl]-1H-imidazole (Example 22, 2.2 g) was treated with 2N KOH (75 mL) and heated at reflux for 12 hours. The resulting solution was cooled on an ice bath and treated dropwise with concentrated aqueous HCl (8 mL) followed by dropwise addition of aqueous 10% citric acid (50 mL). The resulting precipitate was collected by filtration and then it was partitioned between ethyl acetate and 10% citric acid. The organic layer was washed with brine, dried over anhydrous magnesium sulfate and concentrated on a rotary evaporator, keeping the temperature below 25° C. to give a foam. This foam was dissolved in ether-CH2Cl2 (1:1) and diluted to turbidity with hexanes. Evaporation of solvents as above gives the title compound as a colorless powder. MS (FAB, thioglycerol) 454 (m+1), 410 (m-CO2 +1).

Provenance & Evidence