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

HRID 2305660Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2305660
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-5e55f5dfa5cc4800817fdb576eaf9310
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06441005B1

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