Water → HCID 86759786, compound

HRID 896588Notes

Reaction equation

HRID 896588 reaction equation
[CH3:1][C:2]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[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[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30].C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:6]([CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[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 69732576HCID 69732576, compound

Product 1

HCID 86759786HCID 86759786, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Methyl-3-naphthylcarbonyl-5-phenylimidazolidine-2,4-dione (800 mg) was dissolved in DMF (8 mL) and tert-butyl bromoacetate (452 mg) was added. Potassium carbonate (336 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 recrystallization with IPE afforded 704 mg of white crystals.

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 recrystallization with IPE afforded 704 mg of white crystals

Sources & evidence

ORD record
ord-4a6f848b46b84f8ba0f0aaaca14a595a
Source dataset
uspto-grants-2005_07
Patent number
US06919365B2

Reaction notes

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