Hydrochloric Acid → HCID 178440107, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4.86 g of 4-chloro-2-propyl-1-[[2'-(tetrazol-5-yl)biphenyl-4-yl]methyl]imidazole-5-carboxylic acid in 115 mL of tetrahydrofuran at 25° C. is added 2.25 g of carbonyl diimidazole, and the resulting solution is stirred at 25° C. for 3 hours. To the solution is added 3.94 g of tyramine and 23 mL of 2-propanol, and the mixture was stirred at 25° C. for an additional 3 hours. The reaction mixture is poured into water, and the resulting emulsion is adjusted to pH 3 employing hydrochloric acid and then extracted with chloroform. The combined extracts are washed with water and brine, dried over anhydrous sodium sulfate, and concentrated. Column chromatography (elution: 10% 2- propanol/chloroform) affords 3.15 g of the product as an amorphous solid. NMR (300 MHz, DMSO-d6) δ 8.07 (t, 1H, J=8 Hz), 7.69-7.50 (m, 4H), 7.07-6.99 (m, 6H), 6.65 (d, 2H, J=8 Hz), 5.42 (s, 2H), 3.36 (quart., 2H, J=7 Hz), 2.63 (t, 2H, J=7 Hz), 2.50 (t, 2H, J=7 Hz), 1.51 (sext., 2H, J=7 Hz), 0.82 (t, 3H, J=7 Hz).

Provenance & Evidence