Sodium Hydroxide → HCID 57305400, compound

HRID 1590181Notes

Reaction equation

HRID 1590181 reaction equation
[CH2:1]([CH:8]([CH2:15][C:16]([N:18]1[CH2:26][C@H:25]2[C@H:20]([CH2:21][CH:22]=[CH:23][CH2:24]2)[CH2:19]1)=[O:17])[C:9]([O:11]CCC)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([CH:8]([CH2:15][C:16]([N:18]1[CH2:19][C@H:20]2[C@H:25]([CH2:24][CH:23]=[CH:22][CH2:21]2)[CH2:26]1)=[O:17])[C:9]([OH:11])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57049395HCID 57049395, compound

Product 1

HCID 57305400HCID 57305400, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of propyl 2-benzyl-3-(cis-3a,4,7,7a-tetrahydro-2-isoindolinylcarbonyl)propionate (198 mg) in ethanol (2 ml) was added 1N sodium hydroxide solution (668 μl) and the mixture was stirred at room temperature for 16 hours. After the solvent was evaporated under reduced pressure, the residue was dissolved in water and extracted with ethyl acetate. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine and dried over MgSO4. After the solvent was evaporated under reduced pressure, the residue was crystallized from diethyl ether to give 120 mg of 2-benzyl-3-(cis-3a,4,7,7a-tetrahydro-2-isoindolinylcarbonyl)propionic acid.

Workup

  1. customAfter the solvent was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over MgSO4
  7. customAfter the solvent was evaporated under reduced pressure
  8. customthe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-173b1d0a5799431ba3120b1f1059ef52
Source dataset
uspto-grants-1993_04
Patent number
US05202335

Reaction notes

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