Methyl iodide → HCID 66881079, compound

HRID 1893594Notes

Reaction equation

HRID 1893594 reaction equation
[CH2:1]([O:3][C:4](=[O:31])[CH2:5][N:6]([CH2:17][C:18]([N:20]([N:22]1[CH2:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23]1)[CH3:21])=[O:19])[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[CH3:16])[NH:12][N:11]=[CH:10]2)[CH3:2].[H-].[Na+].[CH3:34]I>CN(C)C=O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>[CH2:1]([O:3][C:4](=[O:31])[CH2:5][N:6]([CH2:17][C:18]([N:20]([N:22]1[CH2:23][C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:30]1)[CH3:21])=[O:19])[C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][C:15]=1[CH3:16])[N:12]([CH3:34])[N:11]=[CH:10]2)[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66881861HCID 66881861, compound

Product 1

HCID 66881079HCID 66881079, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 311Citric AcidSolventHCID 6228DimethylformamideSolvent

Procedure

The compound (871 mg, 2.07 mmol) of step B was dissolved in N,N-dimethylformamide (19 ml), 60% sodium hydride (109 mg, 2.73 mmol) was added under ice-cooling with stirring, and the mixture was stirred at the same temperature for 1 hr. Then, methyl iodide (0.44 ml) was added, and the mixture was stirred under ice-cooling for 90 min. The reaction mixture was diluted with 10% citric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine, and dried over anhydrous magnesium sulfate. The insoluble material was filtered off, and the solution was concentrated under reduced pressure. The obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane→ethyl acetate-methanol) to give the title compound (653 mg, yield 73%) as a colorless amorphous solid.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred at the same temperature for 1 hr
  3. stirringthe mixture was stirred under ice-
  4. temperaturecooling for 90 min
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed with saturated aqueous sodium hydrogen carbonate and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationThe insoluble material was filtered off
  9. concentrationthe solution was concentrated under reduced pressure
  10. customThe obtained oil was purified by silica gel column chromatography (ethyl acetate-hexane→ethyl acetate-methanol)

Sources & evidence

ORD record
ord-ca384df60a6848f2880e456393703f3d
Source dataset
uspto-grants-2013_08
Patent number
US08513235B2

Reaction notes

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