Potassium Carbonate → HCID 57519117, compound

HRID 1785356Notes

Reaction equation

HRID 1785356 reaction equation
[CH3:1][N:2]([CH3:27])[C:3]([O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C@@H:12]([CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH3:26])[CH:20]=1)[NH:11][CH2:10][CH2:9]2)=[O:4].FC(F)(F)C(N)=O.C(=O)([O-])[O-].[K+].[K+].C(=O)([O-])O.[Na+]>CO>[CH3:27][N:2]([CH3:1])[C:3](=[O:4])[O:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][CH:15]=1)[C@@H:12]([CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[C:21]([CH3:26])[CH:20]=1)[NH:11][CH2:10][CH2:9]2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 86610739HCID 86610739, compound

Product 1

HCID 57519117HCID 57519117, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 6-dimethylcarbamoyloxy-1-(R)-(2-(4-chloro-3-methylphenoxy)ethyl)-3,4-dihydro-1H-isoquinoline-trifluoroacetamide (154 mg, 0.54 mmol) obtained in step (f) of Example 190 in methanol (1 ml) was added gradually 1M aqueous solution of potassium carbonate (1 ml) with stirring under cooling in a water-bath. The resulting mixture was stirred at 40° C., and after confirming the disappearance of the starting material by thin layer chromatography, the reaction temperature was cooled to ambient temperature, and saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture with stirring. The resulting mixture was extracted with ethyl acetate, and the extract was washed with saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfate and evaporated in vacuo. The residue obtained was purified by chromatography on a silica gel column using a mixed solvent of ethyl acetate and methanol (2:1) as the eluent to afford the title compound (90 mg, yield: 73%) as a pale yellow oil.

Workup

  1. temperatureunder cooling in a water-bath
  2. stirringThe resulting mixture was stirred at 40° C.
  3. stirringwith stirring
  4. extractionThe resulting mixture was extracted with ethyl acetate
  5. washthe extract was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo
  8. customThe residue obtained
  9. customwas purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-76a387b2ef5c457f8bbfa6c0686fdd49
Source dataset
uspto-grants-2009_03
Patent number
US07504437B2

Reaction notes

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