Hydrochloric Acid → 1-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyano-4-(alpha-hydroxybenzyl)imidazole

HRID 52888Notes

Reaction equation

HRID 52888 reaction equation
[BH4-].[Na+].[C:3]([C:11]1[N:12]=[C:13]([CH2:38][CH2:39][CH2:40][CH3:41])[N:14]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=3[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[CH:21][CH:20]=2)[C:15]=1[C:16]#[N:17])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.Cl.[Cl-].[Na+]>C(O)C.C(OCC)(=O)C>[C:34]([O:33][C:31]([C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=1[C:22]1[CH:23]=[CH:24][C:19]([CH2:18][N:14]2[C:15]([C:16]#[N:17])=[C:11]([CH:3]([OH:10])[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)[N:12]=[C:13]2[CH2:38][CH2:39][CH2:40][CH3:41])=[CH:20][CH:21]=1)=[O:32])([CH3:37])([CH3:36])[CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 4311764Sodium borohydrideHCID 190360884-Benzoyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazole

Product 1

HCID 190361771-[(2'-t-Butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyano-4-(alpha-hydroxybenzyl)imidazoleYield 84.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

50.5 mg of sodium borohydride were added to a solution of 691 mg of 4-benzoyl-1-[(2'-t-butoxycarbonylbiphenyl-4-yl)methyl]-2-butyl-5-cyanoimidazole [prepared as described in step (a) above] in 10 ml of ethanol, and the resulting mixture was stirred at room temperature for 1 hour. The reaction mixture was then neutralized with aqueous hydrochloric acid, after which it was mixed with ethyl acetate and with a saturated aqueous solution of sodium chloride. The ethyl acetate layer was separated, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography through silica gel, using a 1:1 by volume mixture of hexane and ethyl acetate as the eluent, to give 589 mg of the title compound as a colorless amorphous solid.

Workup

  1. customThe ethyl acetate layer was separated
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationconcentrated by evaporation under reduced pressure
  4. customThe residue was purified by column chromatography through silica gel
  5. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-38991e6f6bda47a7a36af5cb8fd7a748
Source dataset
uspto-grants-1997_04
Patent number
US05616599

Reaction notes

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