Hydrochloric Acid → 2-(4-Methylbenzyl)-3-(cis-3a,4,7,7a-tetrahydro-2-isoindolinylcarbonyl)propionic acid

HRID 1590183Notes

Reaction equation

HRID 1590183 reaction equation
[CH3:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][CH:7]([CH2:20][C:21]([N:23]2[CH2:31][C@H:30]3[C@H:25]([CH2:26][CH:27]=[CH:28][CH2:29]3)[CH2:24]2)=[O:22])[C:8]([O:10]C2C=CC([N+]([O-])=O)=CC=2)=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH:7]([CH2:20][C:21]([N:23]2[CH2:31][C@H:30]3[C@H:25]([CH2:26][CH:27]=[CH:28][CH2:29]3)[CH2:24]2)=[O:22])[C:8]([OH:10])=[O:9])=[CH:32][CH:33]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 677591944-Nitrophenyl 2-(4-methylbenzyl)-3-(cis-3a,4,7,7a-tetrahydro-2-isoindolinylcarbonyl)propionate

Product 1

HCID 677581832-(4-Methylbenzyl)-3-(cis-3a,4,7,7a-tetrahydro-2-isoindolinylcarbonyl)propionic acidYield 32.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 4-nitrophenyl 2-(4-methylbenzyl)-3-(cis-3a,4,7,7a-tetrahydro-2-isoindolinylcarbonyl)propionate (1.7 g) in methanol (10 ml) was added 1N sodium hydroxide solution (8.0 ml) and the mixture was stirred at room temperature for 15 hours. The reaction mixture was acidified with 1N hydrochloric acid under ice-cooling 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 purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2/1) to give 0.4 g of 2-(4-methylbenzyl)-3-(cis-3a,4,7,7a-tetrahydro-2-isoindolinylcarbonyl)propionic acid as a colorless crystal.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. customAfter the solvent was evaporated under reduced pressure
  6. customthe residue was purified by column chromatography on silica gel eluting with hexane/ethyl acetate (2/1)

Sources & evidence

ORD record
ord-1a9f310f457842b6b4fa43a29b0c7350
Source dataset
uspto-grants-1993_04
Patent number
US05202335

Reaction notes

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