8-Fluorociprofloxacin → 1-Cyclopropyl-8-ethoxy-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid

HRID 1111465

Reaktionsgleichung

Reaktionsgleichung von HRID 1111465
[O-:1][CH2:2][CH3:3].[Na+].[Na].[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:26])=[C:16]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[C:17]=3F)[C:12](=[O:27])[C:11]([C:28]([OH:30])=[O:29])=[CH:10]2)[CH2:8][CH2:7]1>C(O)C>[CH:6]1([N:9]2[C:18]3[C:13](=[CH:14][C:15]([F:26])=[C:16]([N:20]4[CH2:21][CH2:22][NH:23][CH2:24][CH2:25]4)[C:17]=3[O:1][CH2:2][CH3:3])[C:12](=[O:27])[C:11]([C:28]([OH:30])=[O:29])=[CH:10]2)[CH2:7][CH2:8]1

Komponenten

5

Edukt 3

HCID 1228488-FluorociprofloxacinHCID 2723922Sodium ethoxideHCID 5360545Sodium

Produkt 1

HCID 4845751-Cyclopropyl-8-ethoxy-6-fluoro-4-oxo-7-piperazin-1-ylquinoline-3-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of sodium ethoxide prepare from sodium (0.75 g) and absolute ethanol (30 ml) was added 1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-3-quinolinecarboxylic acid (0.8 g) and the mixture in sealed tube was stirred for 52 hours at 140° to 150° C. and then concentrated. Water (60 ml) was added to the residue, and the solution was adjusted pH 7 with acetic acid and and extracted with chloroform. The chloroform layer was washed with saturated saline solution, dried over anhydrous sodium sulfate and then concentrated. The resulting residue was purified by silica gel column chromatography eluting with chloroform-methanol (2:1)→chloroform-methanol-concentrated aqueous ammonia (20:6:1→10:10:1) and recrystallized from ethanol to give the title compound (75 mg) as light brown prisms, mp 119°-122° C.

Aufarbeitung

  1. concentrationconcentrated
  2. additionWater (60 ml) was added to the residue
  3. extractionextracted with chloroform
  4. washThe chloroform layer was washed with saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated
  7. customThe resulting residue was purified by silica gel column chromatography
  8. washeluting with chloroform-methanol (2:1)→chloroform-methanol-concentrated aqueous ammonia (20:6:1→10:10:1)
  9. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-9216f9bff4b8417d837377c818b3be8e
Quelldatensatz
uspto-grants-1990_12
Patentnummer
US04980470

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