Water → HCID 66792911, compound

HRID 534992Notes

Reaction equation

HRID 534992 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](=[O:28])[C:18]([NH:20][C:21]2[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][CH:22]=2)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:30][C:31]([O:33][CH3:34])=[O:32].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[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](=[O:28])[C:18]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([O:27][CH2:30][C:31]([O:33][CH3:34])=[O:32])=[CH:25][CH:26]=2)=[O:19])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 66792759HCID 66792759, compound

Product 1

HCID 66792911HCID 66792911, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-[4-(2-tert-butylphenyl)piperazin-1-yl]-N-(4-hydroxyphenyl)-2-oxoacetamide (Example 199, 0.40 g, 1.05 mmol), methyl bromoacetate (0.18 g, 1.15 mmol) and potassium carbonate (0.29 g, 2.1 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 3 h. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20 to 35:65) to give the title compound (0.32 g, 67%) as a colorless amorphous.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate 80:20 to 35:65)

Sources & evidence

ORD record
ord-3fa4208a02a541528dc16adc666a66a7
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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