Sodium hydride → Moxifloxacin difluoro methoxy ethyl ester

HRID 1770111

Reaktionsgleichung

Reaktionsgleichung von HRID 1770111
[CH3:1][O:2][C:3]1[C:4](F)=[C:5]([CH:19]=[C:20]([F:23])[C:21]=1[F:22])[C:6]([C:8](=[CH:14][NH:15][CH:16]1[CH2:18][CH2:17]1)[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:7].[H-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[C:21]([F:22])=[C:20]([F:23])[CH:19]=[C:5]2[C:4]=1[N:15]([CH:16]1[CH2:18][CH2:17]1)[CH:14]=[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:6]2=[O:7]

Komponenten

4

Edukt 2

HCID 24758Sodium hydrideHCID 178471878HCID 178471878, Verbindung

Produkt 1

HCID 10758239Moxifloxacin difluoro methoxy ethyl esterAusbeute 75 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of ethyl 2-(3-methoxy-2,4,5-trifluorobenzoyl)-3-cyclopropylaminoacrylate (440 mg, 1.29 mmol) in anhydrous tetrahydrofuran (15 mL) at 0° C. was added sodium hydride (62 mg, 1.5 mmol, 1.1 equiv, 60% in mineral oil). The reaction mixture was allowed to stir at 50° C. for 12 hours. The mixture was cooled to room temperature and filtered. The mother liquor was concentrated and a white precipitate formed. The material was collected by suction filtration and air-dried to give 312 mg, 75% yield of a pure white solid, m.p. 178°-181° C.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered
  3. concentrationThe mother liquor was concentrated
  4. customa white precipitate formed
  5. filtrationThe material was collected by suction filtration
  6. customair-dried

Quellen und Nachweise

ORD-Eintrag
ord-5d49d6c7b08743c19637ed2231c32785
Quelldatensatz
uspto-grants-1995_01
Patentnummer
US05385913

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