Acetonitrile → HCID 86672584, compound

HRID 470665Notes

Reaction equation

HRID 470665 reaction equation
[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(#N)C.[Cl:31][C:32]1[CH:40]=[C:39]2[C:35]([C:36]3([C@@H:45]([C:46]4[CH:51]=[CH:50][N:49]=[C:48]([Cl:52])[CH:47]=4)[C@H:44]([C:53]([NH:55][C@@H:56]4[CH2:61][CH2:60][C@@H:59]([C:62]([OH:65])([CH3:64])[CH3:63])[O:58][CH2:57]4)=[O:54])[N:43]([C@H](C4C=CC=CC=4)[C@@H](O)C4C=CC=CC=4)[C:42]43[CH2:85][CH2:84][C:83]([CH3:87])([CH3:86])[CH2:82][CH2:81]4)[C:37](=[O:41])[NH:38]2)=[CH:34][CH:33]=1.C(=O)([O-])[O-].[K+].[K+]>O>[Cl:31][C:32]1[CH:40]=[C:39]2[C:35]([C@@:36]3([C@@H:45]([C:46]4[CH:51]=[CH:50][N:49]=[C:48]([Cl:52])[CH:47]=4)[C@H:44]([C:53]([NH:55][C@@H:56]4[CH2:61][CH2:60][C@@H:59]([C:62]([OH:65])([CH3:64])[CH3:63])[O:58][CH2:57]4)=[O:54])[NH:43][C:42]43[CH2:85][CH2:84][C:83]([CH3:87])([CH3:86])[CH2:82][CH2:81]4)[C:37](=[O:41])[NH:38]2)=[CH:34][CH:33]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 180504Ceric ammonium nitrateHCID 86672585HCID 86672585, compound

Product 1

HCID 86672584HCID 86672584, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Cerium (IV) diammonium nitrate (132 mg, 0.24 mmol) was added to an acetonitrile (10 ml)/water (3 ml) solution of the compound (98 mg, 0.12 mmol) obtained in Step 1 above under ice cooling and the resulting mixture was stirred for 10 minutes. Potassium carbonate (65 mg, 0.48 mmol) was added to the reaction mixture and insoluble matter was removed by filtration through celite. The filtrate was diluted with ethyl acetate, washed with brine and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, the residue was dissolved in chloroform (9 ml) and methanol (1 ml), silica gel (980 mg) was added and the resulting mixture was stirred overnight at room temperature. Insoluble matter was removed by filtration and the residue was purified by NH-silica gel column chromatography (chloroform) to give 39 mg (53%) of the title compound as a colorless solid.

Workup

  1. customwas 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 under reduced pressure
  6. dissolutionthe residue was dissolved in chloroform (9 ml)
  7. additionmethanol (1 ml), silica gel (980 mg) was added
  8. stirringthe resulting mixture was stirred overnight at room temperature
  9. customInsoluble matter was removed by filtration
  10. customthe residue was purified by NH-silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-eaca5dd88ecb4b11a5e04b1d999125d1
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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