Lithium Hydroxide → 2-(3,3-Bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid

HRID 1667123Notes

Reaction equation

HRID 1667123 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14]([O:16]CC)=[O:15])[C:9]2=[O:19])=[CH:4][CH:3]=1.[OH-].[Li+]>C(O)C.O>[F:26][C:23]1[CH:22]=[CH:21][C:20]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:12][CH2:11][N:10]([CH2:13][C:14]([OH:16])=[O:15])[C:9]2=[O:19])=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67358887Ethyl 2-(3,3-bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetate

Product 1

HCID 673571912-(3,3-Bis(4-fluorophenyl)-2-oxopyrrolidin-1-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

The product from Example 58C (0.90 g, 2.50 mmol) was dissolved in ethanol (20 mL). A solution of lithium hydroxide (0.57 g, 23.97 mmol) in water (5 mL) was added, and the reaction was heated to 80° C. for 2 hours. The reaction mixture was cooled to room temperature, concentrated, neutralized with 2 N HCl, and then extracted with ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulfate, filtered, and concentrated to supply the title compound. MS (APCI+) m/z 332.2 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to supply the title compound

Sources & evidence

ORD record
ord-bc7cdfc5ebda47b5af34e72c7fdfb6c2
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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