Potassium Carbonate → HCID 178423629, compound

HRID 470662Notes

Reaction equation

HRID 470662 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][CH: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]([OH:33])[CH2:29][CH2:28]4)=[O:25])[N:13]([C@H](C4C=CC=CC=4)[C@@H](O)C4C=CC=CC=4)[C:12]43[CH2:53][CH2:52][C:51]([CH3:55])([CH3:54])[CH2:50][CH2:49]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][CH: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]([OH:33])[CH2:29][CH2:28]4)=[O:25])[NH:13][C:12]43[CH2:49][CH2:50][C:51]([CH3:55])([CH3:54])[CH2:52][CH2:53]4)[C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 180504Ceric ammonium nitrateHCID 178423625HCID 178423625, compound

Product 1

HCID 178423629HCID 178423629, compoundYield 53%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

The compound (230 mg, 0.29 mmol) obtained in Step 2 above was dissolved in acetonitrile (10 ml) and water (3 ml), cerium (IV) diammonium nitrate (318 mg, 0.58 mmol) was added under ice cooling and the resulting mixture was stirred for 10 minutes. Potassium carbonate (160 mg, 1.16 mmol) was added to the reaction mixture, the resulting mixture was stirred and then 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 and the residue was purified by silica gel column chromatography [chloroform:methanol=100:0→30:1→20:1 (v/v)] to give 90 mg (53%) of the title compound as a pale yellow solid.

Workup

  1. stirringthe resulting mixture was stirred
  2. custominsoluble matter was removed by filtration through celite
  3. additionThe filtrate was diluted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel column chromatography [chloroform:methanol=100:0→30:1→20:1 (v/v)]

Sources & evidence

ORD record
ord-7726dea755c846ddb417740716970ba9
Source dataset
uspto-grants-2014_01
Patent number
US08629133B2

Reaction notes

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