Sulfuric Acid → 4-Amino-4-methylpentanoic acid

HRID 851757Notes

Reaction equation

HRID 851757 reaction equation
[CH3:1][C:2]1([CH3:8])[NH:6][C:5](=[O:7])[CH2:4][CH2:3]1.[OH-].[Ba+2].[OH-].S(=O)(=O)(O)[OH:13].C(=O)([O-])[O-].[Ba+2]>O>[NH2:6][C:2]([CH3:8])([CH3:1])[CH2:3][CH2:4][C:5]([OH:13])=[O:7]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 10563Barium CarbonateHCID 6093286Barium hydroxideHCID 111262105,5-Dimethylpyrrolidin-2-one

Product 1

HCID 2280694-Amino-4-methylpentanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

For example, a mixture of 5,5-dimethyl-2-pyrrolidone, an excess amount of barium hydroxide and a sufficient amount of water is heated under reflux until the reaction is substantially complete. The cooled solution is made slightly acidic with sulfuric acid and neutralized with solid barium carbonate or other bases. After removal of solids by filtration, the filtrate is evaporated under reduced pressure to yield a crude product which after three recrystallizations from an inert solvent such as aqueous ethanol gives an analytically pure product of 4-amino-4,4-dimethyl butanoic acid (4-amino-4-methylvaleric acid). 4-amino-2,4-dimethylvaleric acid is prepared similarly from 3,5,5-trimethyl-2-pyrrolidone.

Workup

  1. temperatureunder reflux until the reaction
  2. customAfter removal of solids
  3. filtrationby filtration
  4. customthe filtrate is evaporated under reduced pressure
  5. customto yield a crude product which
  6. customafter three recrystallizations from an inert solvent such as aqueous ethanol

Sources & evidence

ORD record
ord-52ea6fc441664654a6e13527b7f1c0a6
Source dataset
uspto-grants-1983_05
Patent number
US04386103

Reaction notes

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