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

HRID 2408853Notes

Reaction equation

HRID 2408853 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:20]3[CH:25]=[CH:24][C:23]([Cl: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>[Cl:26][C:23]1[CH:22]=[CH:21][C:20]([C:8]2([C:5]3[CH:4]=[CH:3][C:2]([Cl: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

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67386419Ethyl 2-(3,3-bis(4-chlorophenyl)-2-oxopyrrolidin-1-yl)acetate

Product 1

HCID 673873472-(3,3-Bis(4-chlorophenyl)-2-oxopyrrolidin-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

The product from Example 25C (0.95 g, 2.42 mmol) was dissolved in ethanol/water (4:1, 50 mL) and treated with lithium hydroxide (7.85 g, 328.0 mmol). After stirring for 3 hours at reflux, the reaction was concentrated, diluted with ice/water (50 mL) and neutralized with 1 N HCl. The resulting precipitate was collected by filtration, washed with water (50 mL) and air-dried to afford the title compound.

Workup

  1. temperatureat reflux
  2. concentrationthe reaction was concentrated
  3. additiondiluted with ice/water (50 mL)
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water (50 mL)
  6. customair-dried

Sources & evidence

ORD record
ord-c708e6a4b6134b2cafd82b42893238be
Source dataset
uspto-grants-2014_08
Patent number
US08815869B2

Reaction notes

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