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

HRID 747210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 747210
[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]

Komponenten

5

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76299Silver trifluoroacetateKatalysatorHCID 22555007Acetonitrile chloroformLösungsmittel

Versuchsvorschrift

[(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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-be68cb7fb38c48559f7522e153fb400c
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07396847B2

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