Dimethyl Sulfate → HCID 70212997, compound

HRID 1720253Notes

Reaction equation

HRID 1720253 reaction equation
[CH3:1][N:2]([CH3:19])[C@H:3]1[CH2:16][C@@H:15]([CH3:17])[O:14][CH:5]([O:6][CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C@@H:4]1[OH:18].[H-].[Na+].[CH3:22]OS(OC)(=O)=O>O1CCCC1.C(OCC)(=O)C.O>[CH3:22][O:18][C@@H:4]1[C@@H:3]([N:2]([CH3:1])[CH3:19])[CH2:16][C@@H:15]([CH3:17])[O:14][CH:5]1[O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 3

HCID 6497Dimethyl SulfateHCID 24758Sodium hydrideHCID 70211142HCID 70211142, compound

Product 1

HCID 70212997HCID 70212997, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Benzyl 3,4,6-trideoxy-3-(dimethylamino)-D-xylohexopyranoside (Korte, F., A. Bilow and R. Heinz, Tetrahedron, 1962, 18, 657,666, 10.01 g, 38.06 mmoles) was dissolved in tetrahydrofuran (300 mL) with stirring at room temperature under an argon atmosphere. The solution was treated with small portions of sodium hydride (60% oil dispersion, 1.83 g, 45.68 mmoles). After one hour, dimethylsulfate (5.28 g, 41.87 mmoles) was added and the reaction mixture was stirred for two hours. The reaction mixture was quenched by the careful addition of water and the solution was evaporated in vacuo leaving an oily residue which was resuspended in ethyl acetate and water. The organic layer was separated, dried (MgSO4) and filtered to afford 9.74 g (93%) of the title compound as a slightly yellow oil which solidified on standing.

Workup

  1. stirringthe reaction mixture was stirred for two hours
  2. customThe reaction mixture was quenched by the careful addition of water
  3. customthe solution was evaporated in vacuo
  4. customleaving an oily residue which
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered

Sources & evidence

ORD record
ord-5273325d85984aa3bdf397b08835df64
Source dataset
uspto-grants-1996_04
Patent number
US05506233

Reaction notes

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