Iodine → [(5R)-3-(4-Iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate

HRID 747210Notes

Reaction equation

HRID 747210 reaction equation
[CH3:1][S:2]([O:5][CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:8]1)(=[O:4])=[O:3].[I:19]I>C(Cl)(Cl)Cl.C(#N)C.FC(F)(F)C([O-])=O.[Ag+]>[CH3:1][S:2]([O:5][CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([I:19])=[CH:15][CH:14]=2)[CH2:8]1)(=[O:3])=[O:4]

Participants

5

Reactant 2

HCID 807IodineHCID 15034707[(5r)-3-Phenyl-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate

Product 1

HCID 24744103[(5R)-3-(4-Iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonateYield 53%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 22555007Acetonitrile chloroformSolvent

Procedure

[(5R)-3-phenyl-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate (41 g, 152 mmol) was dissolved in chloroform/acetonitrile (250/250 ml). Silver trifluoroacetate (50 g, 228 mmol) was added followed by portionwise addition of iodine (58 g, 228 mmol). After stirring the reaction overnight, the silver iodide was filtered off, and the filtrate was washed with solutions of 5% sodium thiosulfate (2×500 ml), saturated sodium bicarbonate (500 ml), brine, and dried over magnesium sulfate. The dried solution was evaorated to give the desired product as a yellow solid (32 g) that was used without further purification.

Workup

  1. customthe reaction overnight
  2. filtrationthe silver iodide was filtered off
  3. washthe filtrate was washed with solutions of 5% sodium thiosulfate (2×500 ml), saturated sodium bicarbonate (500 ml), brine
  4. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-be68cb7fb38c48559f7522e153fb400c
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

Loading…