Dimethyl Sulfate → HCID 59317168, compound

HRID 2427169Notes

Reaction equation

HRID 2427169 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@:12]([CH2:21][OH:22])([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[NH:11][C:10]2=[O:23])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:24](=O)([O-])[O-].[K+].[K+].COS(OC)(=O)=O>CN(C)C=O.O.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]2[C:13](=[O:14])[C@@:12]([CH2:21][OH:22])([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:11]([CH3:24])[C:10]2=[O:23])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

7

Reactant 3

HCID 6497Dimethyl SulfateHCID 11430Potassium CarbonateHCID 67253234HCID 67253234, compound

Product 1

HCID 59317168HCID 59317168, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

150 mg of (S)-1-(3,4-Dichlorophenyl)-4-hydroxymethyl-4-phenylimidazolidine-2,5-dione are dissolved in 5 mL of dimethylformamide then 165 mg of potassium carbonate are added followed by 137 μL of dimethylsulfate. The mixture is stirred overnight at room temperature then it is taken in a mixture of water and ethyl acetate. The aqueous phase is extracted with ethyl acetate. The extracts are washed with brine, dried over magnesium sulfate and evaporated to dryness. The residue is purified over silica gel while eluting with a gradient mixture from heptane to pure ethyl acetate to provide the expected product.

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. washThe extracts are washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated to dryness
  5. customThe residue is purified over silica gel
  6. washwhile eluting with a gradient mixture from heptane to pure ethyl acetate

Sources & evidence

ORD record
ord-b1e487da268d48f7a0f1ef86049c12b7
Source dataset
uspto-grants-2011_06
Patent number
US07968581B2

Reaction notes

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