Iodine chloride → [(5R)-3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl acetate

HRID 2374466Notes

Reaction equation

HRID 2374466 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2].[I:19]Cl>C(O)(=O)C>[C:1]([O:4][CH2:5][C@@H:6]1[O:10][C:9](=[O:11])[N:8]([C:12]2[CH:17]=[CH:16][C:15]([I:19])=[C:14]([F:18])[CH:13]=2)[CH2:7]1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 24640Iodine chlorideHCID 20788912[(5R)-3-(3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl acetate

Product 1

HCID 20788911[(5R)-3-(3-fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5(R)-acetoxymethyl-3-(3-fluorophenyl)oxazolidin-2-one (6.33 g) in acetic acid (40 mL) was added iodine monochloride (1.91 mL), the mixture was stirred at room temperature for 18 hours, and then concentrated in vacuo. The resulting residue was dissolved with ethyl acetate, the mixture was washed with aqueous sodium hydrogencarbonate solution, 20% sodium sulfite solution and brine, dried over anhydrous sodium sulfate, filtered, and then concentrated in vacuo to give crude 5(R)-acetoxymethyl-3-(3-fluoro-4-iodophenyl)oxazolidin-2-one (9.48 g).

Workup

  1. concentrationconcentrated in vacuo
  2. dissolutionThe resulting residue was dissolved with ethyl acetate
  3. washthe mixture was washed with aqueous sodium hydrogencarbonate solution, 20% sodium sulfite solution and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-106b3d5c995d4095aed624a1e7491eb9
Source dataset
uspto-grants-2008_12
Patent number
US07462633B2

Reaction notes

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