Dimethyl Sulfate → HCID 59317168, compound

HRID 389909Notes

Reaction equation

HRID 389909 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-001efa0605254db3acb274c6a88a9817
Source dataset
uspto-grants-2013_02
Patent number
US08383608B2

Reaction notes

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