Sodium hydride → HCID 66792833, compound

HRID 534925Notes

Reaction equation

HRID 534925 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([CH:19]2[NH:23][C:22](=[O:24])[CH2:21][CH2:20]2)=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>CN(C=O)C>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17]([CH:19]2[CH2:20][CH2:21][C:22](=[O:24])[N:23]2[CH2:28][C:29]([O:31][CH3:32])=[O:30])=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 66750924HCID 66750924, compound

Product 1

HCID 66792833HCID 66792833, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 5-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}pyrrolidin-2-one obtained in Example 62 (0.40 g, 1.21 mmol) in DMF (7 mL) was added sodium hydride (54 mg, 60% in mineral oil, 1.34 mmol) and the mixture was stirred at room temperature for 30 min. After this time, to the mixture was added methyl bromoacetate (0.20 g, 1.34 mmol) and the mixture was stirred at room temperature for 2 h. The reaction was quenched with saturated ammonium chloride solution, and the mixture was partitioned between ethyl acetate and water, and the organic layer was washed with water, saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was washed with hexane-diisopropyl ether solution to give the title compound (0.41 g, 84%) as a white amorphous solid.

Workup

  1. stirringthe mixture was stirred at room temperature for 2 h
  2. customThe reaction was quenched with saturated ammonium chloride solution
  3. customthe mixture was partitioned between ethyl acetate and water
  4. washthe organic layer was washed with water, saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. washThe resulting residue was washed with hexane-diisopropyl ether solution

Sources & evidence

ORD record
ord-01dfa7cb0778437d95cf16d8413a5c7b
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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