Dimethyl Sulfate → HCID 20083173, compound

HRID 1609076Notes

Reaction equation

HRID 1609076 reaction equation
[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]2[C:13](=[O:21])[C:14]([C:16]([O:18][CH2:19]C)=[O:17])=[CH:15][N:7]3[C:8]=2[C:3]=1[CH2:4][CH:5]([CH3:22])[NH:6]3.S(OC)(O[CH3:27])(=O)=O.C(=O)([O-])[O-].[K+].[K+]>>[F:1][C:2]1[C:11]([F:12])=[CH:10][C:9]2[C:13](=[O:21])[C:14]([C:16]([O:18][CH3:19])=[O:17])=[CH:15][N:7]3[C:8]=2[C:3]=1[CH2:4][CH:5]([CH3:22])[N:6]3[CH3:27]

Participants

4

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 20083162HCID 20083162, compound

Product 1

HCID 20083173HCID 20083173, compoundYield 57.3%

Conditions

Temperature
120 °C

Procedure

To 1.45 g (4.7 mmol) of the compound (155) obtained in Example 33, 10 ml (109 mmol) of dimethyl sulfate was added, and the solution was heated 3.5 hours at 120° C. After air-cooling, to 90 ml of ice/water containing 15 g (109 mmol) of anhydrous potassium carbonate, the solution was added, and the solution was stirred overnight. 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 column chromatography (silica gel 8 g, eluent solvent; chloroform:methanol=100:1) to obtain 830 mg of the subject compound (156) in a 57% yield.

Workup

  1. additionthe solution was added
  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 column chromatography (silica gel 8 g, eluent solvent; chloroform:methanol=100:1)

Sources & evidence

ORD record
ord-3518e67460374f868d1d3896013afa42
Source dataset
uspto-grants-1995_03
Patent number
US05399553

Reaction notes

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