Dimethyl Sulfate → HCID 53758088, compound

HRID 1033636Notes

Reaction equation

HRID 1033636 reaction equation
[CH3:1][O:2][C:3]([C:5]1(CCC)[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([O:15][CH2:16][CH2:17][CH2:18][O:19][C:20]3[CH:25]=[CH:24][C:23]([C:26]([N:28]4[CH2:32][CH2:31][CH2:30][CH2:29]4)=[O:27])=[C:22]([OH:33])[C:21]=3[CH2:34][CH:35]=[CH2:36])=[CH:14][C:7]=2[O:6]1)=[O:4].S(OC)(O[CH3:44])(=O)=O.[OH-].[K+]>C1COCC1>[CH3:44][O:33][C:22]1[C:21]([CH2:34][CH:35]=[CH2:36])=[C:20]([CH:25]=[CH:24][C:23]=1[C:26]([N:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)=[O:27])[O:19][CH2:18][CH2:17][CH2:16][O:15][C:13]1[CH:12]=[CH:11][C:8]2[CH2:9][CH2:10][CH:5]([C:3]([O:2][CH3:1])=[O:4])[O:6][C:7]=2[CH:14]=1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 19917189HCID 19917189, compound

Product 1

HCID 53758088HCID 53758088, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 27 (280 mg, 0.51 mmol) dimethyl sulfate (192 mg, 153 mmol) and potassium hydroxide (57 mg, 1 mmol) was added to about 20 ml of THF, and the reaction mixture was stirred overnight at room temperature. The reaction mixture was 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 75% ethyl acetate/hexane as eluant gave the product.

Workup

  1. washThe reaction mixture was 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-a7076f07058542a88bea01a6881c17a9
Source dataset
uspto-grants-1994_05
Patent number
US05310951

Reaction notes

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