Methanol → N-iso-butoxycarbonyl-2,3-dimethylmaleimide

HRID 921487Notes

Reaction equation

HRID 921487 reaction equation
Cl[C:2]([O:4][CH2:5][CH:6]([CH3:8])[CH3:7])=[O:3].[CH3:9][C:10]1[C:11]([NH:13][C:14](=[O:17])[C:15]=1[CH3:16])=[O:12].C(N(CC)CC)C.CO>CN(C)C=O.C(Cl)(Cl)Cl>[CH2:5]([O:4][C:2]([N:13]1[C:14](=[O:17])[C:15]([CH3:16])=[C:10]([CH3:9])[C:11]1=[O:12])=[O:3])[CH:6]([CH3:8])[CH3:7]

Participants

7

Reactant 4

HCID 887MethanolHCID 8471TriethylamineHCID 287932,3-DimethylmaleimideHCID 62365Isobutyl chloroformate

Product 1

HCID 23628597N-iso-butoxycarbonyl-2,3-dimethylmaleimideYield 83%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

iso-Butyl chloroformate (0.13 ml, 1 mmol) was added dropwise to a stirred solution of 2,3-dimethylmaleimide (0.1 g, 0.8 mmol) and triethylamine (0.13 ml, 0.92 mmol) in dimethylformamide (1.5 ml) at 0-5° C. The reaction mixture was allowed to warm to room temperature and stand for 4 h. Methyl alcohol (0.5 ml) was added, diluted with chloroform (5 ml) and washed with water (3×3 ml). The chloroform solution was dried (Na2SO4) and concentrated in vacuum to give N-iso-butoxycarbonyl-2,3-dimethylmaleimide (yield 83%).

Workup

  1. washwashed with water (3×3 ml)
  2. dry with materialThe chloroform solution was dried (Na2SO4)
  3. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-b4a860452b16455a8e81f8a6c820330f
Source dataset
uspto-grants-2016_03
Patent number
US09273304B2

Reaction notes

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