Dimethyl Sulfate → HCID 15341820, compound

HRID 893463Notes

Reaction equation

HRID 893463 reaction equation
[NH2:1][C:2]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[C:14]([CH2:26][CH2:27][CH3:28])=[C:15]([CH:23]=[CH:24][CH:25]=2)[O:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[OH:34])=[O:3].[OH-].[K+].S(OC)(O[CH3:41])(=O)=O.C1COCC1>C(OCC)(=O)C.CCCCCC.O>[NH2:1][C:2]([C:4]1[CH:30]=[CH:29][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[C:14]([CH2:26][CH2:27][CH3:28])=[C:15]([CH:23]=[CH:24][CH:25]=2)[O:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:6]([CH2:31][CH2:32][CH3:33])[C:5]=1[O:34][CH3:41])=[O:3]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 15341819HCID 15341819, compound

Product 1

HCID 15341820HCID 15341820, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The compound of Example 41 (134 mg), potassium hydroxide (18 mg) and dimethyl sulfate (53 mg) were added to 2.0 ml of THF and the reaction mixture was stirred at room temperature overnight. Water (10 ml) was added, and the reaction mixture was extracted three times with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, filtered, and the solvent was removed under vacuum to give an oil. Chromatography of the oil on silica gel with 50/50 ethyl acetate/hexane as eluant gave the product as a colorless gum.

Workup

  1. extractionthe reaction mixture was extracted three times with ethyl acetate
  2. dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was removed under vacuum
  5. customto give an oil

Sources & evidence

ORD record
ord-012a862aac0a417fbe59acd48e577089
Source dataset
uspto-grants-1992_06
Patent number
US05124350

Reaction notes

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