Sodium Hydroxide → 4-Oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butyric acid

HRID 892614Notes

Reaction equation

HRID 892614 reaction equation
C[O:2][C:3](=[O:18])[CH2:4][CH2:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16].[OH-].[Na+]>CO>[O:17]=[C:6]([NH:7][CH2:8][CH2:9][CH2:10][N:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16])[CH2:5][CH2:4][C:3]([OH:18])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 539702434-Oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butyric acid methyl ester

Product 1

HCID 198959194-Oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butyric acidYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butyric acid methyl ester (900 mg) in methanol (10 ml) was added 2N sodium hydroxide (3 ml) under ice-cooling and the mixture was stirred at room temperature for 4 hours. The reaction mixture was concentrated, and the residue was dissolved in water and washed with ether. The aqueous layer was adjusted to pH 5 with 1N hydrochloric acid, and concentrated to dryness. Chloroform was added to the residue and the insoluble materials were filtered off. The filtrate was concentrated to give 850 mg of 4-oxo-4-[3-(2-oxo-1-pyrrolidinyl)propylamino]butyric acid.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in water
  4. washwashed with ether
  5. concentrationconcentrated to dryness
  6. additionChloroform was added to the residue
  7. filtrationthe insoluble materials were filtered off
  8. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-4e324c2b9c094d2588280a8d8c469f20
Source dataset
uspto-grants-1992_06
Patent number
US05118811

Reaction notes

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