Sodium Bicarbonate → HCID 86705171, compound

HRID 2401269Notes

Reaction equation

HRID 2401269 reaction equation
COC1C=CC([N:9]2[CH2:13][C@H:12]([CH2:14][CH2:15][CH3:16])[N:11]([CH2:17][C:18]([NH:20][C:21]3[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][N:22]=3)=[O:19])[C:10]2=[O:31])=CC=1.[N+]([O-])([O-])=O.[Ce].[NH4+].C(=O)([O-])O.[Na+]>C(#N)C.O>[O:31]=[C:10]1[NH:9][CH2:13][C@H:12]([CH2:14][CH2:15][CH3:16])[N:11]1[CH2:17][C:18]([NH:20][C:21]1[CH:26]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:24]=[CH:23][N:22]=1)=[O:19]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 57418452Ammonium cerium-nitrate2×HCID 86705172HCID 86705172, compound

Product 1

HCID 86705171HCID 86705171, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-[(5S)-3-(4-methoxyphenyl)-2-oxo-5-propylimidazolidin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]acetamide (137 mg) in acetonitrile (3 mL) was cooled in ice, and a solution of ammonium cerium nitrate (340 mg) in water (3 mL) was added dropwise thereto. After stirring the mixture at room temperature for 2 hr, an additional solution of ammonium cerium nitrate (100 mg) in water (0.5 mL) was added thereto, and the mixture was stirred at room temperature for 10 min. Saturated aqueous sodium hydrogen carbonate solution was added thereto, the resulting mixture was extracted with ethyl acetate, and then the organic layer was washed with brine, followed by drying over anhydrous magnesium sulfate. After the dissicant was filterred off, the solvent was distilled off under reduced pressure, and the residue was purified by column chromatography (silica gel cartridge, chloroform/methanol=98:2-80:20) to afford the title compound (76 mg). (ESI pos.) m/z: 331 ([M+H]+)

Workup

  1. temperaturewas cooled in ice
  2. stirringthe mixture was stirred at room temperature for 10 min
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washthe organic layer was washed with brine
  5. dry with materialby drying over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customthe residue was purified by column chromatography (silica gel cartridge, chloroform/methanol=98:2-80:20)

Sources & evidence

ORD record
ord-5baade9e1f584ec7a66b49c321838aa2
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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