Dimethyl Sulfate → HCID 11667588, compound

HRID 1178311Notes

Reaction equation

HRID 1178311 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[O:24][C:23]([CH3:26])([CH3:25])[CH:22]=[CH:21][C:5]2=[C:6]2[C:15]=1[C:14](=[O:16])[C:13]1[C:8](=[CH:9][CH:10]=[C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]3=1)[NH:7]2.[H-].[Na+].[CH3:29]OS(OC)(=O)=O>CN(C)C=O>[CH3:29][O:1][C:2]1[CH:3]=[C:4]2[O:24][C:23]([CH3:26])([CH3:25])[CH:22]=[CH:21][C:5]2=[C:6]2[C:15]=1[C:14](=[O:16])[C:13]1[C:8](=[CH:9][CH:10]=[C:11]3[CH:20]=[CH:19][CH:18]=[CH:17][C:12]3=1)[NH:7]2

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 11233200HCID 11233200, compound

Product 1

HCID 11667588HCID 11667588, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 300 mg of compound of Example 1 in 15 ml of anhydrous dimethylformamide is added dropwise to a suspension of 125 mg of sodium hydride in 10 ml of anhydrous dimethylformamide previously cooled to 0° C. The reaction mixture is maintained at 0° C. for 15 minutes, at room temperature for 30 minutes and then 0.57 ml of dimethylsulfate are added. After 17 hours, the reaction mixture is poured into 150 ml of ice-cold water and extracted with dichloromethane (3×50 ml). The combined organic phases are dried over anhydrous sodium sulphate and then filtered and evaporated to dryness under reduced pressure. Chromatography over silica gel (cyclohexane and then a gradient of acetone 5 to 20%) allowing the expected product to be obtained.

Workup

  1. temperatureThe reaction mixture is maintained at 0° C. for 15 minutes, at room temperature for 30 minutes
  2. extractionextracted with dichloromethane (3×50 ml)
  3. dry with materialThe combined organic phases are dried over anhydrous sodium sulphate
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. customto be obtained

Sources & evidence

ORD record
ord-f61cdc76acb54dcf899901ed389959c0
Source dataset
uspto-grants-2007_10
Patent number
US07276512B2

Reaction notes

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