Potassium Fluoride → (5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-fluoromethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one

HRID 459020

Reaktionsgleichung

Reaktionsgleichung von HRID 459020
[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH2:20]Br)[N:17]=[N:16]3)[O:11][C:10]2=[O:22])[CH:5]=[CH:6][C:7]=1[I:8].[F-].[K+].[F:25][B-](F)(F)F.C([N+]1C=CN(C)C=1)CCC>C(#N)C.O.C(OCC)(=O)C>[F:1][C:2]1[CH:3]=[C:4]([N:9]2[CH2:13][C@H:12]([CH2:14][N:15]3[CH:19]=[C:18]([CH2:20][F:25])[N:17]=[N:16]3)[O:11][C:10]2=[O:22])[CH:5]=[CH:6][C:7]=1[I:8]

Komponenten

7

Edukt 3

HCID 522689Potassium FluorideHCID 27341781-Butyl-3-methylimidazolium tetrafluoroborateHCID 58822461HCID 58822461, Verbindung2×

Produkt 1

HCID 58822460(5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-fluoromethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-oneAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

(5R)-3-(3-Fluoro-4-iodophenyl)-5-[(4-bromomethyl-1H-1,2,3-triazol-1-yl)methyl]oxazolidin-2-one (Intermediate 17, 6.94 g, 14.4 mmol) was dissolved/suspended in acetonitrile (250 mL) and water (1.5 mL). Potassium fluoride (4.19 g, 72.1 mmol) was added, followed by addition of 1-butyl-3-methylimidazolium tetrafluoroborate (18.4 mL) and the solution was heated to 90° C. over night. It was diluted with ethyl acetate, washed with water and dried over magnesium sulfate. Chromatography on silica gel with ethyl acetate gave 2.7 g (45%) of the title compound as an off-white solid.

Aufarbeitung

  1. washwashed with water
  2. dry with materialdried over magnesium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-59bc19a313014abd889ce5c5dc1b0897
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192974B2

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