Methanol → HCID 86698165, compound

HRID 623873Notes

Reaction equation

HRID 623873 reaction equation
[CH3:1][C:2]([CH3:32])([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[NH:21][C:22]([C:25]([CH3:31])([CH3:30])[C:26]([F:29])([F:28])[F:27])=[CH:23][N:24]=3)=[CH:16][N:15]=2)=[CH:10][CH:9]=1)[C:3]([OH:5])=[O:4].[OH-].[Na+:34].CO>C(#N)C>[CH3:1][C:2]([CH3:32])([CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[NH:21][C:22]([C:25]([CH3:31])([CH3:30])[C:26]([F:29])([F:27])[F:28])=[CH:23][N:24]=3)=[CH:16][N:15]=2)=[CH:10][CH:9]=1)[C:3]([O-:5])=[O:4].[Na+:34]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57410855HCID 57410855, compound

Product 1

HCID 86698165HCID 86698165, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

In acetonitrile (4 mL) was suspended 2,2-dimethyl-3-(4-{5-[5-(2,2,2-trifluoro-1,1-dimethylethyl)-1H-imidazol-2-yl]pyridin-2-yl}phenoxy)propanoic acid (175 mg), and 2N aqueous sodium hydroxide solution (391 μL) was added dropwise to the suspension. After adding acetonitrile (1 mL), the reaction mixture was stirred at room temperature overnight. Methanol was added until the reaction mixture became uniform solution, and tar-state insoluble material was separated by filtration. The filtrate was concentrated under reduced pressure, and the obtained solid residue was pulverized by ether, collected by filtration, washed with ether, and dried at room temperature in vacuum to obtain sodium 2,2-dimethyl-3-(4-{5-[5-(2,2,2-trifluoro-1,1-dimethylethyl)-1H-imidazol-2-yl]pyridin-2-yl}phenoxy)propanoate (174 mg).

Workup

  1. additionwas added dropwise to the suspension
  2. customwas separated by filtration
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. filtrationcollected by filtration
  5. washwashed with ether
  6. customdried at room temperature in vacuum

Sources & evidence

ORD record
ord-420cf919346242cd9e74e6f519ecce02
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

Loading…