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Levofloxacin → Levofloxacin Hydrate

HRID 31376
Notes
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Reaction equation

HRID 31376 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>CCC(C)=O>[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

3

Reactant 1

HCID 149096Levofloxacin

Product 1

HCID 3033924Levofloxacin HydrateYield 84%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
-5 °C

Procedure

1.5 g of levofloxacin crude was put in suspension in 15 ml of MEK. The mixture was heated to reflux temperature until complete dissolution of the material. Then the solution was cooled to −5° C. over a period of 3 hours. The precipitate was filtrated under vacuum, washed with 1.5 ml of MEK and dried at 30° C. in a vacuum oven to give 840 mg (84%) of purified levofloxacin hemihydrate.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux temperature
  3. dissolutionuntil complete dissolution of the material
  4. filtrationThe precipitate was filtrated under vacuum
  5. washwashed with 1.5 ml of MEK
  6. customdried at 30° C. in a vacuum oven

Sources & evidence

ORD record
ord-5ef30b4014b14c6b9ef8a9cf7daa197a
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07425628B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes