Methyl iodide → HCID 10337483, compound

HRID 456799Notes

Reaction equation

HRID 456799 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:13]2[CH2:17][C@H:16]([CH2:18][N:19]3[CH:23]=[CH:22][N:21]=[N:20]3)[O:15][C:14]2=[O:24])[CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[N:10][NH:11][CH:12]=1.[H-].[Na+].I[CH3:28]>CN(C)C=O.O.CS(C)=O>[F:1][C:2]1[CH:3]=[C:4]([N:13]2[CH2:17][C@H:16]([CH2:18][N:19]3[CH:23]=[CH:22][N:21]=[N:20]3)[O:15][C:14]2=[O:24])[CH:5]=[CH:6][C:7]=1[C:8]1[N:9]=[N:10][N:11]([CH3:28])[CH:12]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178519213HCID 178519213, compound

Product 1

HCID 10337483HCID 10337483, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(5R)-3-[3-Fluoro-4-(1H-1,2,3-triazol-4-yl)phenyl]-5-(1H-1,2,3-triazol-1-ylmethyl)-1,3-oxazolidin-2-one (Example 7, 1.7 g, 5.2 mmol) was stirred in N,N-dimethylformamide at 0° C. Sodium hydride (0.40 g, 10 mol) was added and the mixture was stirred for 30 minutes. Iodomethane (0.88 g, 6.2 mmol) was added and the reaction was stirred for three days, slowly warming to room temperature. The mixture was diluted with water and extracted using ethyl acetate. The organic layer was washed with water, dried (magnesium sulfate) and concentrated under vacuum. The residue was recrystallized using ethyl acetate to give a mixture of products (0.42 g) as beige solid. The solid was dissolved in dimethylsulfoxide (5 ml), acetonitrile (12 ml) and water (1 ml) and the isomers were separated using Gilson HPLC.

Workup

  1. stirringthe reaction was stirred for three days
  2. extractionextracted
  3. washThe organic layer was washed with water
  4. dry with materialdried (magnesium sulfate)
  5. concentrationconcentrated under vacuum
  6. customThe residue was recrystallized
  7. customto give
  8. customacetonitrile (12 ml) and water (1 ml) and the isomers were separated

Sources & evidence

ORD record
ord-0be5649996cb45e18bce144d7b46efbd
Source dataset
uspto-grants-2007_03
Patent number
US07186738B2

Reaction notes

Loading…