Water → Compound 3

HRID 1966923Notes

Reaction equation

HRID 1966923 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][OH:14])[O:10][C:9]2=[O:15])[CH:5]=[CH:6][CH:7]=1.[I-:16].O>C(#N)C.[Ag+].FC(F)(F)C([O-])=O>[I:16][C:7]1[CH:6]=[CH:5][C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][OH:14])[O:10][C:9]2=[O:15])=[CH:3][C:2]=1[F:1]

Participants

6

Reactant 3

HCID 962WaterHCID 30165Iodide IonHCID 11229590(R)-3-(3-Fluorophenyl)-5-(hydroxymethyl)oxazolidin-2-one

Product 1

HCID 20788885Compound 3Yield 94%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6342AcetonitrileSolvent

Procedure

In 300 ml of acetonitrile was dissolved 30 g of (R)-3-(3-fluorophenyl)-2-oxo-5-oxazolidinylmethanol prepared in the Preparation example 2, and 46 g of trifluoroacetic acid silver salt (CF3COOAg) and 43 g of iodide were added to the solution. After being stirred for one day at room temperature, the solution was added with water and was extracted with ethyl acetate. The organic layer, thus separated, was washed with brine and dehydrated. And then the residue was filtered, concentrated in vacuo and dried thereby to form the title compound 44 g. Yield 94%.

Workup

  1. additionwere added to the solution
  2. extractionwas extracted with ethyl acetate
  3. customThe organic layer, thus separated
  4. washwas washed with brine
  5. filtrationAnd then the residue was filtered
  6. concentrationconcentrated in vacuo
  7. customdried

Sources & evidence

ORD record
ord-270ce32aaca745c691af17befb7ae8bb
Source dataset
uspto-grants-2013_04
Patent number
US08420676B2

Reaction notes

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