Dimethyl Sulfate → HCID 15237279, compound

HRID 1033629Notes

Reaction equation

HRID 1033629 reaction equation
[CH:1]1([CH2:4][C:5]2[C:32]([OH:33])=[C:31]([C:34]([NH:36][CH3:37])=[O:35])[CH:30]=[CH:29][C:6]=2[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]3[CH2:16][CH2:17][CH:18]([C:20]([O:22][CH3:23])=[O:21])[O:19][C:14]=3[C:13]=2[CH2:26][CH2:27][CH3:28])[CH2:3][CH2:2]1.S(OC)(O[CH3:42])(=O)=O.[OH-].[K+]>C1COCC1>[CH:1]1([CH2:4][C:5]2[C:32]([O:33][CH3:42])=[C:31]([C:34]([NH:36][CH3:37])=[O:35])[CH:30]=[CH:29][C:6]=2[O:7][CH2:8][CH2:9][CH2:10][O:11][C:12]2[CH:25]=[CH:24][C:15]3[CH2:16][CH2:17][CH:18]([C:20]([O:22][CH3:23])=[O:21])[O:19][C:14]=3[C:13]=2[CH2:26][CH2:27][CH3:28])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6497Dimethyl SulfateHCID 14797Potassium HydroxideHCID 15341802HCID 15341802, compound

Product 1

HCID 15237279HCID 15237279, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 17 (20 mg, 0.04 mmol), dimethyl sulfate (0.5 mg, 0.12 mmol), and potassium hydroxide (4.5 mg, 0.08 mmol) were added to about 5 ml of THF, and the reaction mixture was stirred overnight at room temperature. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was separated, dried over magnesium sulfate, and concentrated in vacuo to give the product.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto give the product

Sources & evidence

ORD record
ord-bf2ddc733ab84dbdbce6d4ca56152fdd
Source dataset
uspto-grants-1994_05
Patent number
US05310951

Reaction notes

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