Water → [4-(2-oxopyrrolidin-1-yl)phenyl]acetic acid

HRID 1373239Notes

Reaction equation

HRID 1373239 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:20])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]2[CH2:18][CH2:17][CH2:16][C:15]2=[O:19])=[CH:10][CH:9]=1)C.O.S([O-])(O)(=O)=O.[K+]>O1CCCC1.C(O)C>[O:19]=[C:15]1[CH2:16][CH2:17][CH2:18][N:14]1[C:11]1[CH:12]=[CH:13][C:8]([CH2:7][C:6]([OH:20])=[O:5])=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 516920Potassium bisulfateHCID 21072938HCID 21072938, compound

Product 1

HCID 7130749[4-(2-oxopyrrolidin-1-yl)phenyl]acetic acidYield 58.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Aqueous 1 N sodium hydroxide solution (10 ml, 10 mmols) was added to a solution of ethyl[4-(2-oxopyrrolidin-1-yl)phenyl]acetate (0.97 g, 3.9 mmols) in tetrahydrofuran (20 ml) and ethanol (20 ml). The resulting mixture was stirred at 60° C. for 1 hour. Water was added to the reaction mixture, which was acidified with potassium hydrogensulfate added thereto, and then extracted with ethyl acetate. The extract was washed with water, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the residue was crystallized from hexane/ethanol to give a solid of [4-(2-oxopyrrolidin-1-yl)phenyl]acetic acid (0.5 g, 57%).

Workup

  1. additionadded
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationThis was concentrated under reduced pressure
  6. customthe residue was crystallized from hexane/ethanol

Sources & evidence

ORD record
ord-1012e025c6884ec3a73c2cb36bcaf490
Source dataset
uspto-grants-2007_01
Patent number
US07160887B1

Reaction notes

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