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Levofloxacin → Levofloxacin Hydrate

HRID 31371
Notes
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Reaction equation

HRID 31371 reaction equation
[CH3:1][C@@H:2]1[N:23]2[C:6]3[C:7]([C:19]([C:21]([C:24]([OH:26])=[O:25])=[CH:22]2)=[O:20])=[CH:8][C:9]([F:18])=[C:10]([N:11]2[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]2)[C:5]=3[O:4][CH2:3]1>CCCCO>[CH3:1][C@@H:2]1[N:23]2[CH:22]=[C:21]([C:24]([OH:26])=[O:25])[C:19]([C:7]3=[CH:8][C:9]([F:18])=[C:10]([N:11]4[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]4)[C:5](=[C:6]23)[O:4][CH2:3]1)=[O:20].[CH3:1][C@@H:2]1[N:23]2[CH:22]=[C:21]([C:24]([OH:26])=[O:25])[C:19]([C:7]3=[CH:8][C:9]([F:18])=[C:10]([N:11]4[CH2:16][CH2:15][N:14]([CH3:17])[CH2:13][CH2:12]4)[C:5](=[C:6]23)[O:4][CH2:3]1)=[O:20].[OH2:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 149096Levofloxacin

Product 1

HCID 3033924Levofloxacin HydrateYield 118.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1 g of levofloxacin crude was put in suspension in 7 ml of n-BuOH. The mixture was heated to reflux temperature until complete dissolution of the material. Then the solution was cooled to RT over a period of 2.5 hours. The precipitate was filtrated under vacuum, washed with n-BuOH and dried at 60° C. in a vacuum oven to give 810 mg (81%) of purified levofloxacin hemihydrate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux temperature
  • dissolutionuntil complete dissolution of the material
  • filtrationThe precipitate was filtrated under vacuum
  • washwashed with n-BuOH
  • customdried at 60° C. in a vacuum oven
  • Sources & evidence

    ORD record
    ord-edc8959a3ec14e8e9a416f73ba49e7be
    Source dataset
    uspto-grants-2008_09
    DOI
    10.6084/m9.figshare.5104873.v1
    Patent number
    US07425628B2

    Reaction notes

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    On this pageParticipantsProcedureWorkupSources & evidenceReaction notes