Dimethyl Sulfate → HCID 15341823, compound

HRID 1033643Notes

Reaction equation

HRID 1033643 reaction equation
[OH:1][C:2]1[C:3]([CH2:33][CH2:34][CH3:35])=[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].S(OC)(O[CH3:40])(=O)=O.[OH-].[K+].C1COCC1>C(OCC)(=O)C.CCCCCC.O>[CH3:40][O:1][C:2]1[C:3]([CH2:33][CH2:34][CH3:35])=[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

7

Reactant 4

HCID 6497Dimethyl SulfateHCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 15341822HCID 15341822, compound

Product 1

HCID 15341823HCID 15341823, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The compound of Example 44 (105 mg, 0.2153 mmol), dimethyl sulfate (40.7 mg, 0.3229 mmol) and potassium hydroxide (15 mg, 0.2583 mmol) were added to 2.0 ml of THF. The reaction mixture was stirred at room temperature overnight, and then 10 ml of water was added. The mixture was extracted three times with ethyl acetate, and the extracts were combined and dried over anhydrous magnesium sulfate then 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 mixture was extracted three times with ethyl acetate
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationthen filtered
  4. customthe solvent was removed under vacuum
  5. customto give an oil

Sources & evidence

ORD record
ord-9737038e378144db8f78ab54bfaf7d69
Source dataset
uspto-grants-1994_05
Patent number
US05310951

Reaction notes

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