tert-Butyl (S)-2-((S)-4-(4-bromophenyl)-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetate → tert-Butyl (S)-2-((S)-4-phenyl-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetate

HRID 2230225Notes

Reaction equation

HRID 2230225 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C@@:8]2([CH3:34])[C:12](=[O:13])[N:11]([C@@H:14]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10](=[O:26])[N:9]2[CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:4][CH:3]=1>C(O)C.[Pd]>[C:5]1([C@@:8]2([CH3:34])[C:12](=[O:13])[N:11]([C@@H:14]([CH2:22][CH:23]([CH3:25])[CH3:24])[C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16])[C:10](=[O:26])[N:9]2[CH2:27][C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:4]=[CH:3][CH:2]=[CH:7][CH:6]=1

Participants

4

Reactant 1

HCID 86588630tert-Butyl (S)-2-((S)-4-(4-bromophenyl)-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetate

Product 1

HCID 86588631tert-Butyl (S)-2-((S)-4-phenyl-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)-2-(2-methylpropyl)acetateYield 80.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1.9 g (3.59 mmol) of 169.3 in 190 ml of ethanol were hydrogenated over 76 mg of 10% palladium/carbon for 2 h. The catalyst was filtered off, the solvent was removed in vacuo, the residue was dissolved in ethyl acetate and the solution was washed with a 10% strength sodium hydrogen carbonate solution. The phases were separated and the organic phase was dried over sodium sulfate. After filtration, 1.3 g (80%) of 169.4 were obtained.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in ethyl acetate
  4. washthe solution was washed with a 10% strength sodium hydrogen carbonate solution
  5. customThe phases were separated
  6. dry with materialthe organic phase was dried over sodium sulfate
  7. filtrationAfter filtration

Sources & evidence

ORD record
ord-0ead208627724791891ba9d563ed76b0
Source dataset
uspto-grants-2002_07
Patent number
US06423712B1

Reaction notes

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