4-tert.butyl 1-(4nitrobenzyl) 2(R)-isobutylsuccinate → (R)-2-(2-(tert-Butoxy)-2-oxoethyl)-4-methylpentanoic acid

HRID 982567Notes

Reaction equation

HRID 982567 reaction equation
[CH2:1]([C@H:5]([CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:6]([O:8]CC1C=CC([N+]([O-])=O)=CC=1)=[O:7])[CH:2]([CH3:4])[CH3:3]>C(OCC)(=O)C.[Pd]>[CH2:1]([C@H:5]([CH2:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[C:6]([OH:8])=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 585602894-tert.butyl 1-(4nitrobenzyl) 2(R)-isobutylsuccinate

Product 1

HCID 11085587(R)-2-(2-(tert-Butoxy)-2-oxoethyl)-4-methylpentanoic acidYield 72.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

4.4 g of 4-tert.butyl 1-(4-nitrobenzyl) 2(R)-isobutylsuccinate were dissolved in 50 ml of ethyl acetate and hydrogenated for 3.5 hours at room temperature and atmospheric pressure in the presence of 0.6 g of 5% palladium/carbon. The catalyst was removed by filtration and the solution was extracted three times with cold 2N hydrochloric acid. The organic layer was then washed with water and saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by evaporation and the crude product was purified by chromatography on silica gel using chloroform for the elution. 2.0 g (72%) of 4-tert.butyl hydrogen 2(R)-isobutylsuccinate were obtained in the form of an oil. Rf (System C) 0.65.

Workup

  1. customThe catalyst was removed by filtration
  2. extractionthe solution was extracted three times with cold 2N hydrochloric acid
  3. washThe organic layer was then washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed by evaporation
  6. customthe crude product was purified by chromatography on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-3816d908ce30466ab263fb3e3fd30582
Source dataset
uspto-grants-1991_02
Patent number
US04996358

Reaction notes

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