Water → 4-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-benzamide

HRID 351872Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 351872
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:20]([CH2:23][C@H:24]1[O:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([NH2:38])=[O:37])=[C:32]([F:39])[CH:31]=2)[CH2:25]1)=[N+]=[N-].O>C1COCC1>[NH2:20][CH2:23][C@@H:24]1[O:28][C:27](=[O:29])[N:26]([C:30]2[CH:35]=[CH:34][C:33]([C:36]([NH2:38])=[O:37])=[C:32]([F:39])[CH:31]=2)[CH2:25]1

Komponenten

5

Edukt 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 229662085-(S)-Azidomethyl-3-[4'-aminocarbonyl-3'-fluorophenyl]oxazolidine-2-one

Produkt 1

HCID 229661984-(5(S)-aminomethyl-2-oxo-oxazolidin-3-yl)-2-fluoro-benzamideAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Triphenylphosphine (2.9 g, 11.0 mmol) was added portionwise to a solution of 5-(S)-azidomethyl-3-[4′-aminocarbonyl-3′-fluorophenyl]oxazolidine-2-one (2.8 g, 10.0 mmol) in THF (75 ml) under nitrogen atmosphere. The solution was stirred at 40° C. for 2 h, water (2.0 ml) added, and the reaction mixture was stirred at 40° C. overnight. Solvent was removed under vacuum, and the resulting solid was triturated with ether. Precipitated material was filtered, washed with ether and ethanol and dried under vacuum to afford the product as white crystals (1.7 g, 69%). HPLC Rt=5.0 min. MS (m/z): [M+H]+=254.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at 40° C. overnight
  2. customSolvent was removed under vacuum
  3. customthe resulting solid was triturated with ether
  4. filtrationPrecipitated material was filtered
  5. washwashed with ether and ethanol
  6. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-50aa5b50cbc64c178a50d6767ac66317
Quelldatensatz
uspto-grants-2004_06
Patentnummer
US06743811B2

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