Water → Tert-butyl (5,5-dimethyl-3-naphthylcarbonyl-2,4-dioxoimidazolidinyl)acetate

HRID 896587Notes

Reaction equation

HRID 896587 reaction equation
[CH3:1][C:2]1([CH3:21])[NH:6][C:5](=[O:7])[N:4]([C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[O:9])[C:3]1=[O:20].Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:21])[N:6]([CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:5](=[O:7])[N:4]([C:8]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[CH:13]=[CH:12][CH:11]=2)=[O:9])[C:3]1=[O:20]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 121120155,5-Dimethyl-3-naphthylcarbonylimidazolidine-2,4-dione

Product 1

HCID 12112014Tert-butyl (5,5-dimethyl-3-naphthylcarbonyl-2,4-dioxoimidazolidinyl)acetateYield 70.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5,5-Dimethyl-3-naphthylcarbonylimidazolidine-2,4-dione (686 mg) was dissolved in DMF (5 mL), and tert-butyl bromoacetate (473 mg) was added. Potassium carbonate (352 mg) was further added, and the mixture was stirred at room temperature overnight. After water was added carefully to the reaction solution, ethyl acetate (200 mL) was added, followed by extraction. The resulting organic layer was washed with 1N hydrochloric acid, an aqueous saturated sodium bicarbonate solution and a saturated brine in turn, and dried over anhydrous magnesium sulfate, and the solvent was distilled off. Further purification by silica gel chromatography (hexane:ethyl acetate=2:1) afforded white crystals. The resulting fraction was recrystallized from IPE to obtain 679 mg of white powders.

Workup

  1. additionwas added
  2. extractionfollowed by extraction
  3. washThe resulting organic layer was washed with 1N hydrochloric acid
  4. dry with materialan aqueous saturated sodium bicarbonate solution and a saturated brine in turn, and dried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customFurther purification by silica gel chromatography (hexane:ethyl acetate=2:1)
  7. customafforded white crystals
  8. customThe resulting fraction was recrystallized from IPE

Sources & evidence

ORD record
ord-d77a6942f7a648a89aa1c8b0987ba8bb
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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