Sodium Bicarbonate → HCID 178450128, compound

HRID 1059144Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([C:19]3[N:20]=[CH:21][N:22](C(C4C=CC=CC=4)(C4C=CC=CC=4)C4C=CC=CC=4)[CH:23]=3)([OH:18])[CH:15]([CH3:17])[CH3:16])[CH:9]=2)=[CH:4][CH:3]=1.Cl.N1C=CC=CC=1.C(=O)([O-])O.[Na+]>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([C:19]3[N:20]=[CH:21][NH:22][CH:23]=3)([OH:18])[CH:15]([CH3:17])[CH3:16])[CH:9]=2)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

1-(4′-Chloro[1,1′-biphenyl]-3-yl)-2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanol (0.71 g) and pyridine hydrochloride (0.25 g) were dissolved in methanol (20 ml), and the mixture was stirred at 60° C. for 2 h. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution and the mixture was concentrated. Water and ethyl acetate were added and the mixture was extracted with ethyl acetate. The organic layer was dried and concentrated, and the obtained residue was purified by silica gel column chomatography (eluent, dichloromethane:methanol=40:1). Recrystallization from hexane-ethyl acetate gave the title compound (0.31 g) as a colorless solid.

Workup

concentrationthe mixture was concentrated
additionWater and ethyl acetate were added
extractionthe mixture was extracted with ethyl acetate
customThe organic layer was dried
concentrationconcentrated
customthe obtained residue was purified by silica gel column chomatography (eluent, dichloromethane:methanol=40:1)
customRecrystallization from hexane-ethyl acetate

Sources & evidence

ORD record: ord-a9692b3c177c41cc92753d35db0f7782
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518257B1

Reaction notes

Loading…