1,1'-Carbonyldiimidazole → HCID 86714706, compound

HRID 529221Notes

Reaction equation

HRID 529221 reaction equation
[C:1]([O:5][C:6](=[O:17])[C@H:7]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:18](N1C=CN=C1)([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[O:19]>CN(C)C=O>[C:1]([O:5][C:6](=[O:17])[C@H:7]([CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[NH:8][C:18]([N:20]1[CH:24]=[CH:23][N:22]=[CH:21]1)=[O:19])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 7269469D-aspartic acid di-t-butyl ester

Product 1

HCID 86714706HCID 86714706, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

L-aspartic acid di-tert-butyl ester (0.84 g, 3.0 mmol) and 1,1′-carbonyldiimidazole (2.4 g, 15 mmol) were dissolved in N,N-dimethylformamide (10 ml), and the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, ethyl acetate was added, and the mixture was washed with 1N hydrochloric acid (15 mL) and saturated brine. After drying over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (0.72 g, 2.1 mmol).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, ethyl acetate
  2. additionwas added
  3. washthe mixture was washed with 1N hydrochloric acid (15 mL) and saturated brine
  4. dry with materialAfter drying over anhydrous magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f1718adaf8054d44b7648bec79cf833a
Source dataset
uspto-grants-2016_05
Patent number
US09346821B2

Reaction notes

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