Benzyl Bromide → Benzyl ((S)-4-(4-cyanophenyl)-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)acetate

HRID 2230216Notes

Reaction equation

HRID 2230216 reaction equation
[H-].[Na+].[C:3]([C:5]1[CH:10]=[CH:9][C:8]([C@@:11]2([CH3:22])[C:15](=[O:16])[N:14]([CH2:17][C:18]([OH:20])=[O:19])[C:13](=[O:21])[NH:12]2)=[CH:7][CH:6]=1)#[N:4].[CH2:23](Br)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>CN(C=O)C>[C:3]([C:5]1[CH:6]=[CH:7][C:8]([C@@:11]2([CH3:22])[C:15](=[O:16])[N:14]([CH2:17][C:18]([O:20][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:19])[C:13](=[O:21])[N:12]2[CH2:3][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[CH:9][CH:10]=1)#[N:4]

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10849843((S)-4-(4-cyanophenyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)acetic acid

Product 1

HCID 86588625Benzyl ((S)-4-(4-cyanophenyl)-3-benzyl-4-methyl-2,5-dioxoimidazolidin-1-yl)acetateYield 69%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.73 g (160.8 mmol) of sodium hydride were added to a solution of 20 g (73.1 mmol) of ((S)-4-(4-cyanophenyl)-4-methyl-2,5-dioxoimidazolidin-1-yl)acetic acid in 120 ml of absolute DMF with ice-cooling. After stirring at room temperature for 30 min, 19 ml (160.8 mmol) of benzyl bromide were added. The reaction mixture was stirred at room temperature for 2 h, allowed to stand overnight, the solvent was removed in vacuo and the residue was chromatographed on silica gel using heptane/ethyl acetate (2:1). 11.43 g (35%) of 8.1 were obtained.

Workup

  1. temperaturecooling
  2. stirringThe reaction mixture was stirred at room temperature for 2 h
  3. waitto stand overnight
  4. customthe solvent was removed in vacuo
  5. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-eaecbd1bab7343d6bd335842100703f7
Source dataset
uspto-grants-2002_07
Patent number
US06423712B1

Reaction notes

Loading…