Water → HCID 10108979, compound

HRID 495211Notes

Reaction equation

HRID 495211 reaction equation
[CH2:1]([C:3]1[C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:6]([CH3:18])[NH:5][C:4]=1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH3:2].O.[O:27]=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+]>C1COCC1.CC(O)=O>[CH2:1]([C:3]1[C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[C:6]([CH:18]=[O:27])[NH:5][C:4]=1[C:19]([O:21][C:22]([CH3:24])([CH3:23])[CH3:25])=[O:20])[CH3:2]

Participants

6

Reactant 3

HCID 962Water2×HCID 180504Ceric ammonium nitrateHCID 68954186HCID 68954186, compound

Product 1

HCID 10108979HCID 10108979, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-benzyl 2-tert-butyl 3-ethyl-5-methyl-1H-pyrrole-2,4-dicarboxylate (2.75 mmol) in THF (32 mL), AcOH (40 mL), and H2O (32 mL) was added CAN in one portion. The reaction was stirred at room temperature for 4 hours, then poured into water (500 mL) and extracted with CH2Cl2 (3×100 mL). The combined organic solutions were washed with saturated aqueous sodium bicarbonate (1×200 mL), dried over Na2SO4 and concentrated. Purification by flash chromatography gave a white solid. HRMS (ES) exact mass calcd for C20H23NO5 (M+H+): 358.1649. Found (M+Na+): 380.1478

Workup

  1. extractionextracted with CH2Cl2 (3×100 mL)
  2. washThe combined organic solutions were washed with saturated aqueous sodium bicarbonate (1×200 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customPurification by flash chromatography
  6. customgave a white solid

Sources & evidence

ORD record
ord-a2995c77e6034addbe6d7fcf3ba12bef
Source dataset
uspto-grants-2009_05
Patent number
US07538231B2

Reaction notes

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