Dimethyl Sulfate → HCID 20083109, compound

HRID 1656747Notes

Reaction equation

HRID 1656747 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:12](=[O:20])[C:13]([C:15]([O:17][CH2:18]C)=[O:16])=[CH:14][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][NH:6]3.S(OC)(O[CH3:25])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:12](=[O:20])[C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][N:7]3[C:8]=2[C:3]=1[CH2:4][CH2:5][N:6]3[CH3:25]

Participants

4

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 19788680HCID 19788680, compound

Product 1

HCID 20083109HCID 20083109, compoundYield 46%

Conditions

Temperature
120 °C

Procedure

To 810 mg (2.8 mmol) of the compound (144) obtained in Example 29, 5 ml (55 mmol) of dimethyl sulfate was added, and the solution was heated for at 120° C. for 5.5 hours. After air-cooling, to 45 ml of ice/water containing 7.5 g (55 mmol) of anhydrous potassium carbonate, was added the solution, and was stirred for 1 hour. The solution was extracted with 50 ml of chloroform, and after drying over magnesium sulfate, the solvent was removed by distillation. The residue was separated by the column chromatography (silica gel 8 g, eluent solvent; chloroform:methanol=100:1) to obtain 371 mg of the subject compound (145) in a 46% yield.

Workup

  1. additionwas added the solution
  2. extractionThe solution was extracted with 50 ml of chloroform
  3. dry with materialafter drying over magnesium sulfate
  4. customthe solvent was removed by distillation
  5. customThe residue was separated by the column chromatography (silica gel 8 g, eluent solvent; chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-b22972c66ff347348cd23d866a96ef38
Source dataset
uspto-grants-1993_10
Patent number
US05254685

Reaction notes

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