Dimethyl Sulfate → HCID 15341833, compound

HRID 893473Notes

Reaction equation

HRID 893473 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][CH:32]=[CH2:33])[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][CH:32]=[CH2:33])[C:5]=1[O:34][CH3:41])=[O:3]

Participants

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 15341832HCID 15341832, compound

Product 1

HCID 15341833HCID 15341833, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The compound of Example 54 (132 mg, 0.280 mmol), potassium hydroxide (18.8 mg, 0.336 mmol) and dimethyl sulfate (52.9 mg, 0.420 mmol) were added to THF, and the reaction mixture was stirred overnight at room temperature, then 10 ml of water was added, and the layers were separated. The aqueous layer was extracted three times with ethyl acetate, and the combined organic fractions were dried and filtered. The solvent was removed under vacuum to give an oil. Chromatography of the oil on silica gel with 50/50 ethyl acetate/hexane gave the product as a white solid.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted three times with ethyl acetate
  3. customthe combined organic fractions were dried
  4. filtrationfiltered
  5. customThe solvent was removed under vacuum
  6. customto give an oil

Sources & evidence

ORD record
ord-fc71d34dedf747e6b5fa718b285610f5
Source dataset
uspto-grants-1992_06
Patent number
US05124350

Reaction notes

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