Potassium Carbonate → HCID 86762259, compound

HRID 470676Notes

Reaction equation

HRID 470676 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]3([C@@H:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([Cl:22])[C:17]=4[F:23])[C@H:14]([C:24]([NH:26][C@@H:27]4[CH2:32][CH2:31][C@@H:30]([CH2:33][OH:34])[O:29][CH2:28]4)=[O:25])[N:13]([C@H](C4C=CC=CC=4)[C@@H](O)C4C=CC=CC=4)[C:12]43[CH2:52][C:51]([CH2:55][F:56])([CH2:53][F:54])[CH2:50]4)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[N+]([O-])([O-])=O.[NH4+].[NH4+].[Ce+4].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C@@:6]3([C@@H:15]([C:16]4[CH:21]=[CH:20][N:19]=[C:18]([Cl:22])[C:17]=4[F:23])[C@H:14]([C:24]([NH:26][C@@H:27]4[CH2:32][CH2:31][C@@H:30]([CH2:33][OH:34])[O:29][CH2:28]4)=[O:25])[NH:13][C:12]43[CH2:50][C:51]([CH2:55][F:56])([CH2:53][F:54])[CH2:52]4)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 180504Ceric ammonium nitrateHCID 86762260HCID 86762260, compound

Product 1

HCID 86762259HCID 86762259, compoundYield 57.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The compound (153 mg, 0.19 mmol) obtained in Step 2 above was dissolved in acetonitrile (10 ml) and water (3 ml), cerium (IV) diammonium nitrate (207 mg, 0.38 mmol) was added under ice cooling and the resulting mixture was stirred for 10 minutes. Potassium carbonate (104 mg, 0.76 mmol) was added to the reaction mixture and the precipitated insoluble matter was removed by filtration through celite. The filtrate was diluted with ethyl acetate, washed with brine and dried over anhydrous sodium sulfate. The solvent was evaporated, the residue was purified by NH-silica gel column chromatography (chloroform:methanol=100:0→40:1) and then the residue was dissolved in 2-propanol (10 ml) and stirred at 50° C. for 2 days. The solvent was evaporated under reduced pressure and then the residue was purified by chiral column liquid chromatography [fractionation conditions: CHIRALPAK IC, n-hexane:ethanol=2:3 (v/v)] to give 67 mg (57%) of the title compound as a colorless solid.

Workup

  1. customthe precipitated insoluble matter was removed by filtration through celite
  2. additionThe filtrate was diluted with ethyl acetate
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated
  6. customthe residue was purified by NH-silica gel column chromatography (chloroform:methanol=100:0→40:1)
  7. dissolutionthe residue was dissolved in 2-propanol (10 ml)
  8. stirringstirred at 50° C. for 2 days
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by chiral column liquid chromatography [fractionation conditions: CHIRALPAK IC, n-hexane:ethanol=2:3 (v/v)]

Sources & evidence

ORD record
ord-5493c76b3e044631a062d3c943d3ec1b
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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