Dimethylformamide → HCID 18331382, compound

HRID 2270566Notes

Reaction equation

HRID 2270566 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:15]=[C:14](C)[CH:13]=[C:12]([N+:17]([O-:19])=[O:18])[C:11]=1[OH:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:27]N(C)C=O.[CH2:32](I)[CH3:33]>O.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[C:11]([O:20][CH2:32][CH3:33])=[C:12]([N+:17]([O-:19])=[O:18])[CH:13]=[CH:14][C:15]=1[CH3:27])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 18331368HCID 18331368, compound

Product 1

HCID 18331382HCID 18331382, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of the compound (350 mg) obtained in Example 520b, cesium carbonate (404 mg), dimethylformamide (15 ml) and ethyl iodide (0.4 ml) was stirred at 60° C. for 2 h. To the reaction mixture, ethyl acetate and water were added. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:n-hexane=2:8) to give the titled compound quantitatively.

Workup

  1. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  2. dry with materialdried with anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (eluent, ethyl acetate:n-hexane=2:8)

Sources & evidence

ORD record
ord-d849cbb7befe43ec888cbb0dec0391cf
Source dataset
uspto-grants-2001_12
Patent number
US06331553B1

Reaction notes

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