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Hydrochloric Acid → Finafloxacin hydrochloride

HRID 2302230
Notes
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Reaction equation

HRID 2302230 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 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

Product 1

HCID 11662028Finafloxacin hydrochloride

Reagents, catalysts & solvents 3

HCID 962WaterSolvent
HCID 6342AcetonitrileSolvent
HCID 8471TriethylamineSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8e511d8626114cb6b25eb1cd345ff9cd
Source dataset
uspto-grants-2002_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06432948B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes