Hydrochloric Acid → Moxifloxacin difluoro methoxy ethyl ester

HRID 358879Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 358879
[H-].[Na+].[CH:3]1([NH:6][CH:7]=[C:8]([C:14](=[O:26])[C:15]2[CH:20]=[C:19]([F:21])[C:18]([F:22])=[C:17]([O:23][CH3:24])[C:16]=2F)[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4]1.Cl>O1CCCC1>[CH:3]1([N:6]2[C:16]3[C:15](=[CH:20][C:19]([F:21])=[C:18]([F:22])[C:17]=3[O:23][CH3:24])[C:14](=[O:26])[C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7]2)[CH2:5][CH2:4]1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 178471878HCID 178471878, Verbindung

Produkt 1

HCID 10758239Moxifloxacin difluoro methoxy ethyl esterAusbeute 73,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

150 mg (0.0035 mole) of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 1.20 g (0.0035 mole) of ethyl 3-cyclopropylamino-2-(3-methoxy-2,4,5-trifluorobenzoyl)acrylate (XXXI) [prepared as described in Step (E11) above] in 30 ml of anhydrous tetrahydrofuran, and the mixture was stirred at room temperature for 30 minutes. At the end of this time, the reaction mixture was acidified by adding 1N aqueous hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried, and the solvent was removed by evaporation under reduced pressure to afford 0.83 g of ethyl 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylate (XXXII) as colorless needles, melting at 180°-182° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8437bba81e8e4a898e83cb65d92e0d7a
Quelldatensatz
uspto-grants-1991_03
Patentnummer
US04997943

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