Sodium hydride → HCID 86705167, compound

HRID 2401261Notes

Reaction equation

HRID 2401261 reaction equation
[H-].[Na+].[CH3:3][CH:4]([C@H:6]1[CH2:10][N:9]([C:11]2[CH:12]=[N:13][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:15][CH:16]=2)[C:8](=[O:21])[NH:7]1)[CH3:5].Br[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25].C(=O)([O-])O.[Na+]>CN(C=O)C.O>[O:21]=[C:8]1[N:9]([C:11]2[CH:12]=[N:13][C:14]([C:17]([F:19])([F:18])[F:20])=[CH:15][CH:16]=2)[CH2:10][C@H:6]([CH:4]([CH3:3])[CH3:5])[N:7]1[CH2:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 516892Sodium BicarbonateHCID 86705166HCID 86705166, compound

Product 1

HCID 86705167HCID 86705167, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.53 g) was added to a solution of (4S)-4-(propan-2-yl)-1-[6-(trifluoromethyl)pyridin-3-yl]imidazolidin-2-one (5.6 g) in DMF (20 mL), and the mixture was stirred at room temperature for 10 min. Thereafter, tert-butyl bromoacetate (2.0 mL) was added portionwise thereto, and the mixture was stirred at room temperature for 2 hr. Water and saturated aqueous sodium hydrogen carbonate solution were added thereto, and the mixture was extracted with chloroform. The organic layer was separated out by phase-separation cartridge (Biotage, Isolute Phase Separator) and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate) to afford tert-butyl {(5S)-2-oxo-5-(propan-2-yl)-3-[6-(trifluoromethyl)pyridin-3-yl]imidazolidin-1-yl}acetate (802 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hr
  2. extractionthe mixture was extracted with chloroform
  3. customThe organic layer was separated out by phase-separation cartridge (Biotage, Isolute Phase Separator)
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel cartridge, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-787f39e65c814613829317919a437af2
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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