Sodium Hydroxide → HCID 19595579, compound

HRID 612518Notes

Reaction equation

HRID 612518 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](=[C:19]2\[C:20](=[O:31])[N:21]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])[CH2:22][CH2:23]\2)/[C:9]2[CH:14]=[CH:13][C:12]([S:15]([CH3:18])(=[O:17])=[O:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](/[C:8](=[C:19]2\[C:20](=[O:31])[N:21]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH2:22][CH2:23]\2)/[C:9]2[CH:10]=[CH:11][C:12]([S:15]([CH3:18])(=[O:16])=[O:17])=[CH:13][CH:14]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 9912165HCID 9912165, compound

Product 1

HCID 19595579HCID 19595579, compoundYield 81.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

1 g (0.0045 mole) of ethyl (Z)-3-[3-[1-(4-chlorophenyl)-1-[4-(methylsulphonyl)phenyl]methylene]-2-oxo-pyrrolidin-1-yl]propanoate are placed in a solution in a mixture of 15 ml of ethanol and 20 ml of water and treated with 0.28 g (1.5 eq.) of sodium hydroxide. The medium is heated at 50° C. for 4 h. The ethanol was evaporated off and the aqueous phase is then extracted with ethyl acetate, acidified with a dilute hydrochloric acid solution, and extracted with dichloromethane. The organic phase is washed with water dried and concentrated. The residue is taken up into t-butyl methyl ether. 1.6 g of (Z)-3-[3-[1-(4-chlorophenyl)-1-[4-(methylsulphonyl)phenyl]methylene]-2-oxo-pyrrolidin-1-yl]propanoic acid are thus obtained as a beige solid of melting point 178-179° C.

Workup

  1. customThe ethanol was evaporated off
  2. extractionthe aqueous phase is then extracted with ethyl acetate
  3. extractionextracted with dichloromethane
  4. washThe organic phase is washed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-97d654c93d254e35b40d2055d43193b1
Source dataset
uspto-grants-1999_12
Patent number
US06004994

Reaction notes

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