Water → HCID 18622145, compound

HRID 1861947Notes

Reaction equation

HRID 1861947 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24].O.[CH2:26](I)[CH3:27]>CN(C)C=O>[CH2:26]([O:3][C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:5]=1[CH2:13][N:14]1[C:18](=[O:19])[C:17]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:16]2[C:15]1=[O:24])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 2306330HCID 2306330, compound

Product 1

HCID 18622145HCID 18622145, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of sodium hydride (content, 60%; 36 mg) and anhydrous dimethylformamide (5 ml), a solution of the compound (224 mg) obtained in Example 318 in anhydrous dimethylformamide (3 ml) and ethyl iodide (0.072 ml) were successively added dropwise at 0° C. in a nitrogen atmosphere and stirred at room temperature for 24 h. Water was added to the reaction mixture, which was distilled under reduced pressure; thereafter, ethyl acetate and water were added to the resulting residue. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous sodium sulfate and distilled under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent, n-hexane ethyl acetate=1:1) to give 213 mg of the titled compound (yield, 87%).

Workup

  1. distillationwas distilled under reduced pressure
  2. additionthereafter, ethyl acetate and water were added to the resulting residue
  3. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. distillationdistilled under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent, n-hexane ethyl acetate=1:1)

Sources & evidence

ORD record
ord-e514c8c0952849b68a8bccc2fdadd17a
Source dataset
uspto-grants-2003_03
Patent number
US06534546B1

Reaction notes

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