Dimethyl Sulfate → HCID 20083129, compound

HRID 1609095Notes

Reaction equation

HRID 1609095 reaction equation
[F: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.[CH3:21]OS(OC)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[F: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[CH3:21]

Participants

4

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 20083182HCID 20083182, compound

Product 1

HCID 20083129HCID 20083129, compoundYield 46%

Conditions

Temperature
120 °C

Procedure

To 1.24 g (4.5 mmol) of the compound (189) obtained in Example 62, 8 ml (87 mmol) of dimethylsulfate was added, and the solution was heated at 120° C. for 3 hours. After air-cooling, the solution was added to 70 ml of ice/water to which 12 g (87 mmol) of anhydrous potassium carbonate was added, and the solution was stirred for 1 hour. The solution was extracted with 100 ml of chloroform, and after drying over magnesium sulfate, the solvent was removed by distillation. The residue was separated by column chromatography (silica gel 40 g, eluent solvent; chloroform:methanol=100:1) to obtain 571 mg of the subject compound (190) in a 46% yield.

Workup

  1. temperatureAfter air-cooling
  2. additionwas added
  3. extractionThe solution was extracted with 100 ml of chloroform
  4. dry with materialafter drying over magnesium sulfate
  5. customthe solvent was removed by distillation
  6. customThe residue was separated by column chromatography (silica gel 40 g, eluent solvent; chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-c6500629aeda483a9e3479d0b3c12129
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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