Hydrochloric Acid → HCID 67973331, compound

HRID 623874Notes

Reaction equation

HRID 623874 reaction equation
[CH3:1][C:2]([CH3:38])([CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([C:21]3[N:22]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:37])([CH3:36])[CH3:35])[CH:23]=[C:24]([C:26]([F:29])([F:28])[F:27])[N:25]=3)=[CH:17][CH:16]=2)=[CH:11][N:10]=1)[C:3]([O:5]C)=[O:4].[OH-].[Na+].Cl.C(OCC)(=O)C>C(O)C.[Cl-].[Na+].O>[CH3:1][C:2]([CH3:38])([CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]([C:21]3[N:22]([CH2:30][O:31][CH2:32][CH2:33][Si:34]([CH3:36])([CH3:35])[CH3:37])[CH:23]=[C:24]([C:26]([F:29])([F:27])[F:28])[N:25]=3)=[CH:19][CH:20]=2)=[CH:11][N:10]=1)[C:3]([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86698166HCID 86698166, compound

Product 1

HCID 67973331HCID 67973331, compoundYield 60.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

In ethanol (10 mL) was dissolved methyl 2,2-dimethyl-3-[(5-{4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}pyridin-2-yl]oxy]-propanoate (490 mg), 2N aqueous sodium hydroxide solution (2.2 mL) was added to the solution, and the mixture was stirred at room temperature overnight. The reaction mixture was ice-cooled and neutralized with 2N hydrochloric acid (2.2 mL), then, ethyl acetate and saturated brine were added to the mixture, and the liquids were separated. The organic layer was separated, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 97:3) to obtain 2,2-dimethyl-3-[(5-{4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-pyridin-2-yl)oxy]propanoic acid (287 mg).

Workup

  1. additionwas added to the solution
  2. temperaturecooled
  3. customthe liquids were separated
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (chloroform:methanol=100:0 to 97:3)

Sources & evidence

ORD record
ord-676311665a3e4b108fd2e4cd86d5e368
Source dataset
uspto-grants-2016_04
Patent number
US09302996B2

Reaction notes

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