Hydrochloric Acid → 4-Acetyl-2-butyl-1-[(2'-carboxybiphenyl-4-yl)methyl]-5-cyanoimidazole

HRID 265028Notes

Reaction equation

HRID 265028 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

Reactant 2

HCID 313Hydrochloric AcidHCID 190361124-Acetyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazole

Product 1

HCID 190361394-Acetyl-2-butyl-1-[(2'-carboxybiphenyl-4-yl)methyl]-5-cyanoimidazoleYield 96.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

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).

Workup

  1. concentrationafter which it was concentrated by evaporation under reduced pressure
  2. customThe concentrate was purified by column chromatography through silica gel
  3. additionby volume mixture of methylene chloride and methanol as the eluent
  4. customto give a colorless amorphous solid
  5. customThe solid was triturated in hexane
  6. filtrationcollected by filtration
  7. customdried

Sources & evidence

ORD record
ord-1a323891413a4f80b35cf64981de0863
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

Loading…