Hydrochloric Acid → 4-Acetyl-2-butyl-1-[(2'-carboxybiphenyl-4-yl)methyl]-5-cyanoimidazole
Reaction equation
[C:1]([C:4]1[N:5]=[C:6]([CH2:31][CH2:32][CH2:33][CH3:34])[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([O:26]C(C)(C)C)=[O:25])=[CH:14][CH:13]=2)[C:8]=1[C:9]#[N:10])(=[O:3])[CH3:2].Cl>O1CCOCC1>[C:1]([C:4]1[N:5]=[C:6]([CH2:31][CH2:32][CH2:33][CH3:34])[N:7]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([OH:26])=[O:25])=[CH:14][CH:13]=2)[C:8]=1[C:9]#[N:10])(=[O:3])[CH3:2]Participants
4
Procedure
A solution of 1.3 g of 4-acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazole [prepared as described in step (a) above] in 30 ml of a 4N solution of hydrogen chloride in dioxane was allowed to stand overnight at room temperature, after which it was concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, using a 10:1 by volume mixture of methylene chloride and methanol as the eluent, to give a colorless amorphous solid. The solid was triturated in hexane, collected by filtration and dried, to give 1.1 g of the title compound, melting at above 55° C. (with softening).