Acetic Acid → N-(tert-Butoxycarbonyl) Desethylene Ciprofloxacin

HRID 1270075

Reaktionsgleichung

Reaktionsgleichung von HRID 1270075
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:29])[C:18]([C:26]([OH:28])=[O:27])=[CH:19][N:20]2[CH:23]2[CH2:25][CH2:24]2)=[CH:15][C:14]=1[F:30].C(O)(=O)C>CS(C)=O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:13]1[CH:22]=[C:21]2[C:16]([C:17](=[O:29])[C:18]([C:26]([OH:28])=[O:27])=[CH:19][N:20]2[CH:23]2[CH2:25][CH2:24]2)=[CH:15][C:14]=1[F:30])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 176Acetic AcidHCID 187201N-BOC-ethylenediamineHCID 483180Fluoroquinolonic acid

Produkt 1

HCID 18448980N-(tert-Butoxycarbonyl) Desethylene Ciprofloxacin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

In a sealed tube N-(tert-butoxycarbonyl)ethylenediamine (5 mL) was added to a solution of 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (3 g) in DMSO (6 mL). The reaction mixture was stirred at 110° C. for 15 h. The reaction mixture was allowed to cool at 50° C. and was poured into ice, acetic acid was added to reach pH=5. A precipitate appeared and was separated by filtration and washed with ether to afford a 40:60 mixture of title compounds (4.4 g).

Aufarbeitung

  1. temperatureto cool at 50° C.
  2. additionwas added
  3. customwas separated by filtration
  4. washwashed with ether
  5. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-06c7b110dde7435897f8c57a644940fb
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202221B2

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