Water → HCID 18766538, compound

HRID 480704Notes

Reaction equation

HRID 480704 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([NH2:12])=[O:11].C(=O)([O-])[O-].[K+].[K+].Br[C:20]([CH3:29])([CH3:28])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22].O>C(#N)C>[NH2:12][C:10]([CH2:9][CH2:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[O:1][C:20]([CH3:29])([CH3:28])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[O:11]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 311592-HydroxybenzenepropanamideHCID 90290tert-Butyl 2-bromo-2-methylpropionate

Product 1

HCID 18766538HCID 18766538, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

3-(2-Hydroxyphenyl)propionamide (5.6 g, 33.9 mmol) was dissolved in acetonitrile (15 mL), and potassium carbonate (18.7 g, 135 mmol) was added thereto. Subsequently, tert-butyl 2-bromoisobutyrate (30.3 g, 135 mmol) was added, and the mixture was stirred at 80° C. After completion of reaction, water was added thereto, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, followed by drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=40/1), whereby the target compound was obtained (2.67 g, 26%).

Workup

  1. additionwas added
  2. extractionthe resultant mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialby drying over sodium sulfate, concentration under reduced pressure, and purification by silica gel chromatography (chloroform/methanol=40/1), whereby the target compound
  5. customwas obtained (2.67 g, 26%)

Sources & evidence

ORD record
ord-0afbc53b44054f0e978f3d4fd14d0d6b
Source dataset
uspto-grants-2003_11
Patent number
US06653334B1

Reaction notes

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