Hydrochloric Acid → HCID 178450101, compound

HRID 1059191Notes

Reaction equation

HRID 1059191 reaction equation
[OH:1][C:2]([C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([NH:42][C:43](=[O:45])[CH3:44])[CH:37]=2)=[CH:32][CH:31]=1)([C:6]1[N:7]=[CH:8][N:9](C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:10]=1)[CH2:3][CH:4]=[CH2:5].Cl.C(=O)([O-])O.[Na+]>C(O)C.[C].[Pd]>[OH:1][C:2]([C:30]1[CH:31]=[CH:32][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([NH:42][C:43](=[O:45])[CH3:44])[CH:37]=2)=[CH:34][CH:35]=1)([C:6]1[N:7]=[CH:8][NH:9][CH:10]=1)[CH2:3][CH2:4][CH3:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 18668524HCID 18668524, compound

Product 1

HCID 178450101HCID 178450101, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A suspension of N-[4′-[1-hydroxy-1-(1-trityl-1H-imidazol-4-yl)-3-butenyl][1,1′-biphenyl]-3-yl]acetamide (829 mg), 10% palladium carbon (829 mg) and 1N hydrochloric acid (1.41 ml) in ethanol (14 ml) was stirred under a hydrogen atmosphere at room temperature for 9.5 h. Sodium hydrogen carbonate (130 mg) was added and the mixture was stirred. The reaction mixture was filtered through Celite, and the filtrate was concentrated. The residue was purified by silica gel chomatography (eluent;chloroform→chloroform:methanol=10:1→7:1→4:1) to give the colorless amorphous title compound (420 mg).

Workup

  1. stirringthe mixture was stirred
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel chomatography (eluent;chloroform→chloroform:methanol=10:1→7:1→4:1)

Sources & evidence

ORD record
ord-88651519631348329f70e81bf87c644a
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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