Dimethyl Sulfate → HCID 15341815, compound

HRID 1756204Notes

Reaction equation

HRID 1756204 reaction equation
[OH:1][C:2]1[C:3]([CH2:34][CH2:35][CH3:36])=[C:4]([CH:27]=[CH:28][C:29]=1[C:30]([NH:32][CH3:33])=[O:31])[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:23]=[CH:22][C:13]2[CH2:14][CH2:15][CH:16]([C:18]([O:20][CH3:21])=[O:19])[O:17][C:12]=2[C:11]=1[CH2:24][CH2:25][CH3:26].S(OC)(O[CH3:41])(=O)=O.[OH-].[K+]>C1COCC1>[CH3:41][O:1][C:2]1[C:3]([CH2:34][CH2:35][CH3:36])=[C:4]([CH:27]=[CH:28][C:29]=1[C:30]([NH:32][CH3:33])=[O:31])[O:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:23]=[CH:22][C:13]2[CH2:14][CH2:15][CH:16]([C:18]([O:20][CH3:21])=[O:19])[O:17][C:12]=2[C:11]=1[CH2:24][CH2:25][CH3:26]

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 15341814HCID 15341814, compound

Product 1

HCID 15341815HCID 15341815, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 33 (100 mg, 0.2 mmol), dimethyl sulfate (76 mg, 0.6 mmol), and potassium hydroxide (22 mg, 0.4 mmol) were added to about 15 ml of THF. The reaction mixture was stirred overnight at room temperature then washed with water and thoroughly extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated in vacuo. Chromatography of the crude material on silica gel using 50/50 ethyl acetate/hexane as eluant gave the product.

Workup

  1. washthen washed with water
  2. extractionthoroughly extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dadd0ed4616a448c8d97697735f02e70
Source dataset
uspto-grants-1995_08
Patent number
US05439937

Reaction notes

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