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Hydrochloric Acid → Finafloxacin hydrochloride

HRID 2302230
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2302230
[C:1]([C:3]1[C:4](F)=[C:5]([F:22])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:15][CH2:14]1)[CH:10]=[C:9]([C:16]([O:18]CC)=[O:17])[C:8]2=[O:21])#[N:2].[C@H:24]12[CH2:32][NH:31][CH2:30][C@@H:29]1[NH:28][CH2:27][CH2:26][O:25]2.O.[OH-].[Li+].[ClH:36]>C(#N)C.O.C(N(CC)CC)C>[ClH:36].[C:1]([C:3]1[C:4]([N:31]2[CH2:32][C@H:24]3[C@@H:29]([NH:28][CH2:27][CH2:26][O:25]3)[CH2:30]2)=[C:5]([F:22])[CH:6]=[C:7]2[C:12]=1[N:11]([CH:13]1[CH2:14][CH2:15]1)[CH:10]=[C:9]([C:16]([OH:18])=[O:17])[C:8]2=[O:21])#[N:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 15069982(4aS,7aS)-octahydropyrrolo[3,4-b][1,4]oxazineHCID 18417531Ethyl 8-cyano-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate

Produkt 1

HCID 11662028Finafloxacin hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel
HCID 6342AcetonitrileLösungsmittel
HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

200 mg (0.63 mmol) of ethyl 8-cyano-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylate are stirred under argon at 40-45° C. for 2 hours with 97 mg (0.75 mmol) of (1S,6S)-2-oxa-5,8-diazabicyclo[4.3.0]nonane and 0.17 ml of triethylamine in 3 ml of acetonitrile. All volatile components are removed in vacuo, the residue is treated with water, insoluble material is filtered off and the filtrate is extracted with dichloromethane. The organic phase is dried over sodium sulphate and then concentrated in vacuo. The resulting residue is dissolved in 6 ml of tetrahydrofuran and 2 ml of water and treated with 30 mg (0.72 mmol) of lithium hydroxide monohydrate. After stirring at room temperature for 16 hours, the mixture is acidified with dil. hydrochloric acid and the resulting precipitate is filtered off with suction and dried.

Aufarbeitung

  1. customAll volatile components are removed in vacuo
  2. additionthe residue is treated with water, insoluble material
  3. filtrationis filtered off
  4. extractionthe filtrate is extracted with dichloromethane
  5. dry with materialThe organic phase is dried over sodium sulphate
  6. concentrationconcentrated in vacuo
  7. dissolutionThe resulting residue is dissolved in 6 ml of tetrahydrofuran
  8. filtrationthe resulting precipitate is filtered off with suction
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8e511d8626114cb6b25eb1cd345ff9cd
Quelldatensatz
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06432948B1

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