Iodine → (5R)-3-(3-Fluoro-4-iodophenyl)-5-[4-methyl-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one

HRID 1452569Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1452569
[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][N:14]3[CH:18]=[C:17]([CH3:19])[N:16]=[N:15]3)[O:10][C:9]2=[O:20])[CH:5]=[CH:6][CH:7]=1.[I:21]I>ClCCl.FC(F)(F)C([O-])=O.[Ag+]>[F:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][C@H:11]([CH2:13][N:14]3[CH:18]=[C:17]([CH3:19])[N:16]=[N:15]3)[O:10][C:9]2=[O:20])[CH:5]=[CH:6][C:7]=1[I:21]

Komponenten

5

Edukt 2

HCID 807Iodine2×HCID 58778317(5R)-3-(3-Fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one2×

Produkt 1

HCID 58778315(5R)-3-(3-Fluoro-4-iodophenyl)-5-[4-methyl-1,2,3-triazol-1-ylmethyl]oxazolidin-2-oneAusbeute 42,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 76299Silver trifluoroacetateKatalysator2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Silver trifluoroacetate (0.52 g, 2.35 mmol) was added to a solution of (5R)-3-(3-fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one (Intermediate 14) (0.50 g, 1.81 mmol) in dichloromethane (15 ml). Iodine (0.55 g, 2.17 mmol) was added over 1.5 hours, and it was stirred overnight. After 16 hours, the solids were removed by filtration and additional silver trifluoroacetate (0.38 g, 1.72 mmol) and iodine (0.27 g, 1.06 mmol) were added. After and additional 24 hours, the reaction mixture was filtered. The filter cake was washed with methanol. The methanol filtrate was concentrated under vacuum to give 0.31 g of the title product.

Aufarbeitung

  1. waitAfter 16 hours
  2. additionwere added
  3. filtrationAfter and additional 24 hours, the reaction mixture was filtered
  4. washThe filter cake was washed with methanol
  5. concentrationThe methanol filtrate was concentrated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-5d4b024d1ec34ecbba76904b9c21b5c8
Quelldatensatz
uspto-grants-2009_01
Patentnummer
US07473699B2

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