Tetrahydrofuran → HCID 67975349, compound

HRID 623900Notes

Reaction equation

HRID 623900 reaction equation
C([N:8]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[N:10]=[C:9]1[C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]([CH3:36])([CH3:35])[C:32]([OH:34])=[O:33])=[CH:25][CH:24]=2)=[CH:19][CH:18]=1)C1C=CC=CC=1.O1CCCC1>C(Cl)(Cl)Cl.[OH-].[Pd+2].[OH-].[C]>[F:16][C:13]([F:14])([F:15])[C:11]1[NH:10][C:9]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]([CH3:35])([CH3:36])[C:32]([OH:34])=[O:33])=[CH:25][CH:24]=3)=[CH:19][CH:18]=2)=[N:8][CH:12]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 67975260HCID 67975260, compound

Product 1

HCID 67975349HCID 67975349, compoundYield 93.6%

Reagents, catalysts & solvents 2

HCID 178502593HCID 178502593, compoundCatalystHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

The mixture of 3-({4′-[1-benzyl-4-(trifluoromethyl)-1H-imidazol-2-yl]biphenyl-4-yl}oxy)-2,2-dimethylpropanoic acid (830 mg), 20% palladium hydroxide-carbon (850 mg) and tetrahydrofuran (20 mL) was stirred at 60° C. under hydrogen atmosphere for 6 hours. Nitrogen gas was passed through the reaction mixture, and the mixture was diluted with chloroform. The mixture was filtered by using a membrane filter, and the filtrate was washed with tetrahydrofuran, methanol and chloroform. The filtrates were combined, and n-hexane and propanol were added to the residue obtained by concentrating the same under the reduced pressure. The precipitated solid was collected by filtration to obtain 3-({4′-[5-(trifluoromethyl)-1H-imidazol-2-yl]biphenyl-4-yl}oxy)-2,2-dimethylpropanoic acid (635 mg).

Workup

  1. filtrationThe mixture was filtered
  2. filtrationfilter
  3. washthe filtrate was washed with tetrahydrofuran, methanol and chloroform
  4. additionn-hexane and propanol were added to the residue
  5. customobtained
  6. concentrationby concentrating the same under the reduced pressure
  7. filtrationThe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-14d651d6b0e34d53bc5a422c8b229a21
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

Loading…