Hydrochloric Acid → HCID 68507960, compound

HRID 2243201Notes

Reaction equation

HRID 2243201 reaction equation
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]2[CH2:15][C:14]([CH3:17])([CH3:16])[CH:13]([O:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]#[N:26])=[C:21]([C:27]([F:30])([F:29])[F:28])[CH:20]=3)[C:12]2=[O:31])[CH:5]=1.[OH-].[Na+].Cl>C1COCC1>[C:25]([C:22]1[CH:23]=[CH:24][C:19]([O:18][CH:13]2[C:14]([CH3:17])([CH3:16])[CH2:15][N:11]([CH2:10][C:6]3[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=3)[C:3]([OH:32])=[O:2])[C:12]2=[O:31])=[CH:20][C:21]=1[C:27]([F:30])([F:29])[F:28])#[N:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 68507392HCID 68507392, compound2×

Product 1

HCID 68507960HCID 68507960, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound obtained in Example 25, (±)-3-[3-(4-cyano-3-trifluoromethyl-phenoxy)-4,4-dimethyl-2-oxo-pyrrolidin-1-ylmethyl]-benzoic acid methyl ester, (0.128 g, 0.29 mmol) was dissolved in 4 mL THF and 1.0 mL 1 M NaOH was added. The reaction was stirred at ambient temperature overnight. The reaction mixture was acidified with 1 N HCl to pH ˜3 and extracted into ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate and concentrated in vacuo. The material was triturated with diethyl ether and filtered to obtain the carboxylic acid as a white solid (0.105 g, 85%).

Workup

  1. extractionextracted into ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe material was triturated with diethyl ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-05d19252cd044cc3997d24ed0539b3b8
Source dataset
uspto-grants-2010_03
Patent number
US07674819B2

Reaction notes

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