N-(Methoxycarbonyl)maleimide → HCID 70977734, compound

HRID 882581Notes

Reaction equation

HRID 882581 reaction equation
CO[C:3]([N:5]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]1=[O:11])=O.NC[CH2:14][C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=[O:17]>C(=O)([O-])O.[Na+]>[O:10]=[C:9]1[CH:8]=[CH:7][C:6](=[O:11])[N:5]1[CH2:3][CH2:14][C:15]([CH3:20])([CH3:19])[C:16]([OH:18])=[O:17]

Participants

4

Reactant 2

HCID 580610N-(Methoxycarbonyl)maleimideHCID 15020294-amino-2,2-dimethylbutanoic acid

Product 1

HCID 70977734HCID 70977734, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a solution of 1.39 g (8.95 mmol) of N-methoxycarbonylmaleimide in 44 ml of saturated sodium hydrogencarbonate solution were added, at 0° C., 1.5 g (8.95 mmol) of 4-amino-2,2-dimethylbutyric acid, and the mixture was stirred for 40 min. Subsequently, the cooling bath was removed and the reaction mixture was stirred for a further 1 h. While cooling with ice, the reaction mixture was then adjusted to pH 3 by adding sulphuric acid, and extracted with ethyl acetate. The combined organic phases were dried over magnesium sulphate and concentrated. 1.17 g (79% purity, 49% of theory) of the title compound were obtained.

Workup

  1. customSubsequently, the cooling bath was removed
  2. temperatureWhile cooling with ice
  3. additionby adding sulphuric acid
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic phases were dried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0ccd06af84244e2684ef02a9af51a0d0
Source dataset
uspto-grants-2015_03
Patent number
US08992932B2

Reaction notes

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