Dimethyl Sulfate → HCID 15341830, compound

HRID 893470Notes

Reaction equation

HRID 893470 reaction equation
[OH:1][C:2]1[C:3]([CH2:33][CH:34]=[CH2:35])=[C:4]([CH:26]=[CH:27][C:28]=1[C:29]([NH:31][CH3:32])=[O:30])[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([CH2:23][CH2:24][CH3:25])=[C:12]([CH:20]=[CH:21][CH:22]=1)[O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16].[OH-].[K+].S(OC)(O[CH3:42])(=O)=O>C1COCC1>[CH3:42][O:1][C:2]1[C:3]([CH2:33][CH:34]=[CH2:35])=[C:4]([CH:26]=[CH:27][C:28]=1[C:29]([NH:31][CH3:32])=[O:30])[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[C:11]([CH2:23][CH2:24][CH3:25])=[C:12]([CH:20]=[CH:21][CH:22]=1)[O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 15341829HCID 15341829, compound

Product 1

HCID 15341830HCID 15341830, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 51 (120 mg, 0.247 mmol), potassium hydroxide (16.6 mg, 0.285 mmol) and dimethyl sulfate (46.7 mg, 0.37 mmol) were added to 5.0 ml of THF, and the reaction mixture was stirred at room temperature overnight. The solvent was removed under vacuum, and 10 ml of water was added. The solution was extracted three times with ethyl acetate, the combined extracts were dried, and the solvent was removed under vacuum to give an oil. Chromatography of the oil on silica gel using 50/50 ethyl acetate/hexane as eluant gave the product as a colorless gum.

Workup

  1. customThe solvent was removed under vacuum, and 10 ml of water
  2. additionwas added
  3. extractionThe solution was extracted three times with ethyl acetate
  4. customthe combined extracts were dried
  5. customthe solvent was removed under vacuum
  6. customto give an oil

Sources & evidence

ORD record
ord-8adce66fef694bdcb4c40d9d9f9a9cc0
Source dataset
uspto-grants-1992_06
Patent number
US05124350

Reaction notes

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