Sodium Azide → (5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-one

HRID 459009

Reaktionsgleichung

Reaktionsgleichung von HRID 459009
CS(O[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])=[C:15]([F:20])[CH:14]=2)[CH2:8]1)(=O)=O.[N-:21]=[N+:22]=[N-:23].[Na+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[N:21]([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])=[C:15]([F:20])[CH:14]=2)[CH2:8]1)=[N+:22]=[N-:23]

Komponenten

5

Edukt 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 23624705Methanesulfonic acid (5R)-3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester2×

Produkt 1

HCID 23626594(5R)-5-(Azidomethyl)-3-(3-fluoro-4-iodophenyl)-1,3-oxazolidin-2-oneAusbeute 88,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

[(5R)-3-(3-Fluoro-4-iodophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate (Intermediate 4, 6.14 g, 14.7 mmol) was dissolved in N,N-dimethylformamide (50 ml). Sodium azide (1.92 g, 29.6 mmol) was added and the reaction was stirred at 75° C. overnight. The yellow mixture was poured into half-saturated sodium bicarbonate and extracted using ethyl acetate. The organic layer was washed three times with water, dried (magnesium sulfate), filtered, and concentrated to give the title compound as a yellow solid (4.72 g).

Aufarbeitung

  1. extractionextracted
  2. washThe organic layer was washed three times with water
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-acfff7b13cf847aa84a0adfd67844734
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07192974B2

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