Water → Levofloxacin Hydrate

HRID 31375

Reaction equation

HRID 31375 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.[OH2:27]>CS(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].[OH2:27]

Participants

4

Reactant 2

HCID 962WaterHCID 149096Levofloxacin

Product 1

HCID 3033924Levofloxacin HydrateYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
108 °C

Procedure

1 g of levofloxacin crude was put in suspension in 1.5 ml of DMSO. The mixture was heated to 108° C. until complete dissolution of the material. Then H2O (7.5 ml) was added over 10 minutes and the mixture was cooled to RT. The precipitate was filtrated under vacuum, washed with 1 ml of a mixture DMSO:H2O 1:5 and dried at 60° C. in an air-flow oven to give 840 mg (84%) of purified levofloxacin hemihydrate.

Workup

  1. temperaturethe mixture was cooled to RT
  2. filtrationThe precipitate was filtrated under vacuum
  3. washwashed with 1 ml of a mixture DMSO:H2O 1:5
  4. customdried at 60° C. in an air-flow oven

Sources & evidence

ORD record
ord-f38215139cb6419da48d0bcd8cd9d6f6
Source dataset
uspto-grants-2008_09
Patent number
US07425628B2

Linked notes

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