Hydrochloric Acid → 2-Acetamido-2,3-dimethylbutanoic acid

HRID 461292Notes

Reaction equation

HRID 461292 reaction equation
[NH2:1][C:2]([CH3:9])([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4].[C:10](OC(=O)C)(=[O:12])[CH3:11].Cl>[OH-].[Na+]>[C:10]([NH:1][C:2]([CH3:9])([CH:6]([CH3:8])[CH3:7])[C:3]([OH:5])=[O:4])(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 2295252-Amino-2,3-dimethylbutanoic acid

Product 1

HCID 2338052-Acetamido-2,3-dimethylbutanoic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

To a stirred solution of 2-amino-2,3-dimethylbutyric acid (13.1 g) in 55 ml 2N NaOH maintained at 5° C is added simultaneously dropwise but separately 17 ml acetic anhydride and 95 ml 2N NaOH so that the pH of the solution is maintained at about 8.5. After stirring at room temperature for a further 1/2 hour, the mixture is acidified with concentrated HCl and the product, (±)-2-acetylamino-2,3-dimethylbutyric acid, removed by filtration, washed with cold water and air-dried. A sample recrystallized from acetonitrile had melting point 189°-190° C.

Workup

  1. additionis added simultaneously dropwise
  2. customthe product, (±)-2-acetylamino-2,3-dimethylbutyric acid, removed by filtration
  3. washwashed with cold water
  4. customair-dried
  5. customA sample recrystallized from acetonitrile

Sources & evidence

ORD record
ord-76b7dfbb330e4112b967c0a27b76dcf4
Source dataset
uspto-grants-1977_12
Patent number
US04062671

Reaction notes

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