HCID 18668597, compound → HCID 178450197, compound

HRID 1059258Notes

Reaction equation

HRID 1059258 reaction equation
C([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)=[CH:13][C:12]([C:22]([C:27]2[N:28]=[CH:29][N:30](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:31]=2)([OH:26])[CH:23]([CH3:25])[CH3:24])=[CH:11][CH:10]=1)C1C=CC=CC=1>CO.[C].[Pd]>[F:21][C:18]1[CH:19]=[CH:20][C:15]([C:14]2[C:9]([OH:8])=[CH:10][CH:11]=[C:12]([C:22]([OH:26])([C:27]3[N:28]=[CH:29][NH:30][CH:31]=3)[CH:23]([CH3:25])[CH3:24])[CH:13]=2)=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 18668597HCID 18668597, compound

Product 1

HCID 178450197HCID 178450197, compoundYield 123.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

A suspension of 1-[6-benzyloxy-4′-fluoro[1,1′-biphenyl]-3-yl]-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (647 mg) and 10% palladium carbon (647 mg) in methanol (15 ml) was stirred under a hydrogen atmosphere at room temperature for 4 h. The reaction mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by silica gel chomatography (eluent; ethyl acetate→ethyl acetate:methanol=20:1). Recrystallization from ethyl acetate-hexane gave the title compound (396 mg) as colorless powder crystals.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel chomatography (eluent; ethyl acetate→ethyl acetate:methanol=20:1)
  4. customRecrystallization from ethyl acetate-hexane

Sources & evidence

ORD record
ord-9a3c77ca9f144b1fbd698f4e36b0a64c
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

Loading…