Acetic Anhydride → Linezolid

HRID 245336

Reaktionsgleichung

Reaktionsgleichung von HRID 245336
[C:1](O)(=[O:3])[CH3:2].[NH2:5][CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)=[C:15]([F:25])[CH:14]=2)[CH2:8]1.C(OC(=O)C)(=O)C>O>[CH3:2][C:1]([NH:5][CH2:6][C@@H:7]1[O:11][C:10](=[O:12])[N:9]([C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:20][CH2:21][O:22][CH2:23][CH2:24]3)=[C:15]([F:25])[CH:14]=2)[CH2:8]1)=[O:3]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 56650010HCID 56650010, Verbindung

Produkt 1

HCID 441401LinezolidAusbeute 88,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

(S)-5-(aminomethyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one acetate (3.5 g, 10 mmol) was dissolved in 20 mL of water. The solution was heated to 50° C. and then acetic anhydride (0.72 g, 12 mmol) was added dropwise and stirred at 50° C. for 2 hours. The mixture was cooled down to 0° C. to crystallize, filtered, washed with water, dried and recrystallized with ethyl acetate to provide 3.0 g of Linezolid in 88% yield.

Aufarbeitung

  1. temperatureThe mixture was cooled down to 0° C.
  2. customto crystallize
  3. filtrationfiltered
  4. washwashed with water
  5. customdried
  6. customrecrystallized with ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-88a3e2ff98284d29809171362a7793e8
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08658789B2

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