Ethyl Acetate → HCID 68584886, compound

HRID 17528Notes

Reaction equation

HRID 17528 reaction equation
[C:1]([C:3]1[C:4](O)=[C:5]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:6]([F:16])=[C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:8]=1[CH3:9])#[N:2].C(OCC)(=O)C.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[C:19]([C:18]1[O:23][C:4]2[C:3]([C:1]#[N:2])=[C:8]([CH3:9])[C:7]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)=[C:6]([F:16])[C:5]=2[N:17]=1)([CH3:21])([CH3:22])[CH3:20]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 516892Sodium BicarbonateHCID 86630869HCID 86630869, compound

Product 1

HCID 68584886HCID 68584886, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

N-(5-Cyano-2-fluoro-4-hydroxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide (I-238) (124 mg, 0.38 mol) was dissolved in toluene (5 ml), and at room temperature, paratoluenesulfonic acid monohydrate (20 mg, 0.11 mmol) was added. The reaction liquid was heated under reflux under nitrogen atmosphere for 4.5 hours. After cooling to room temperature, the solution was fractionated with ethyl acetate and an aqueous saturated sodium hydrogencarbonate solution. The aqueous layer was separated, this was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=9:1) to obtain the entitled compound (106 mg, 90%) as a white solid.

Workup

  1. customThe reaction liquid
  2. temperaturewas heated
  3. temperatureunder reflux under nitrogen atmosphere for 4.5 hours
  4. customThe aqueous layer was separated
  5. extractionthis was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe insoluble matter was separated by filtration
  9. customthe solvent was evaporated away
  10. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-d5f29fa0197c4d488debbdd9019b39d3
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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