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

HRID 2230224Notes

Reaction equation

[CH2:1](Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C@@:18]2([CH3:37])[C:22](=[O:23])[N:21]([C@@H:24]([CH2:32][CH:33]([CH3:35])[CH3:34])[C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[C:20](=[O:36])[NH:19]2)=[CH:14][CH:13]=1>CN(C=O)C>[Br:11][C:12]1[CH:17]=[CH:16][C:15]([C@@:18]2([CH3:37])[C:22](=[O:23])[N:21]([C@@H:24]([CH2:32][CH:33]([CH3:34])[CH3:35])[C:25]([O:27][C:28]([CH3:29])([CH3:30])[CH3:31])=[O:26])[C:20](=[O:36])[N:19]2[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 0 °C

Procedure

540 μl (4.4 mmol) of benzyl bromide and then, at 0° C., 140 mg of a 55-65% strength sodium hydride dispersion in oil were added to a solution of 1.75 g (4 mmol) of 169.2 in 20 ml of absolute DMF and the mixture was stirred at 0° C. for 15 min and at room temperature for 3 h. After allowing to stand overnight, the solvent was removed in vacuo and the residue was chromatographed on silica gel using heptane/ethyl acetate=8/2. The product fractions were combined and the solvent was removed in vacuo. 1.97 g (93%) of 169.3 were obtained.

Workup

waitto stand overnight
customthe solvent was removed in vacuo
customthe residue was chromatographed on silica gel
customthe solvent was removed in vacuo

Sources & evidence

ORD record: ord-e7a752822d2e423e90c6faa6ed512e20
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06423712B1

Reaction notes

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