1-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid → 7-[1-(t-Butoxycarbonylamino)-3-azabicyclo[3.2.0]hept-3-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

HRID 1603437

Reaktionsgleichung

Reaktionsgleichung von HRID 1603437
[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:15][CH2:14][CH:13]1[CH2:12][NH:11][CH2:10]2)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:16]1([N:19]2[C:28]3[C:23](=[CH:24][C:25]([F:31])=[C:26](F)[C:27]=3[F:29])[C:22](=[O:32])[C:21]([C:33]([OH:35])=[O:34])=[CH:20]2)[CH2:18][CH2:17]1>N1C=CC=CC=1>[C:1]([O:5][C:6]([NH:8][C:9]12[CH2:15][CH2:14][CH:13]1[CH2:12][N:11]([C:26]1[C:27]([F:29])=[C:28]3[C:23]([C:22](=[O:32])[C:21]([C:33]([OH:35])=[O:34])=[CH:20][N:19]3[CH:16]3[CH2:18][CH2:17]3)=[CH:24][C:25]=1[F:31])[CH2:10]2)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 5354141-Cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acidHCID 15859786tert-Butyl 3-azabicyclo[3.2.0]heptan-1-ylcarbamate

Produkt 1

HCID 158597877-[1-(t-Butoxycarbonylamino)-3-azabicyclo[3.2.0]hept-3-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

1.9 g of 1-(t-butoxycarbonylamino)-3-azabicyclo[3.2.0]heptane and 0.83 g of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid were added to 15 ml of pyridine, followed by heating under reflux for 4 hours. After the solvent was distilled off under reduced pressure, the resulting residue was purified by silica gel column chromatography (using a 100:1 mixture of chloroform and methanol as the eluent) and recrystallization (from ethyl acetate-diisopropyl ether) to obtain 0.99 g of 7-[1-(t-butoxycarbonylamino)-3-azabicyclo[3.2.0]hept-3-yl]-1-cyclopropyl-6,8-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid (m.p. 211-215° C.).

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 4 hours
  3. distillationAfter the solvent was distilled off under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (
  5. additiona 100:1 mixture of chloroform and methanol as the eluent) and
  6. customrecrystallization (from ethyl acetate-diisopropyl ether)

Quellen und Nachweise

ORD-Eintrag
ord-c81e115d99e94d7dac0cdeef76bfb07c
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05990106

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