Levofloxacin → Levofloxacin Hydrate

HRID 2244557Notes

Reaction equation

HRID 2244557 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>C1(C)C=CC=CC=1.C(Cl)(Cl)Cl>[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]

Participants

3

Reactant 1

HCID 149096Levofloxacin

Product 1

HCID 3033924Levofloxacin Hydrate

Reagents, catalysts & solvents 1

HCID 22987606Toluene trichloromethaneSolvent

Procedure

Levofloxacin crude is dissolved in mixture of toluene-chloroform at temperature of 20° C. to 40° C. by mixing for about 30 min to 2 hrs. Removed the insolubles by filtration, treated the clear solution with carbon and distilled off the toluene-chloroform at temperature below 60° C. Isopropanol is added to the mass, temperature is raised to 65° C. to 90° C., known quantity of water preferably to make-up the water content about 12% to about 20%, more selectively about 15% is added to the reaction mass at temperature of 60° C. to 90° C., mixed for about 5 min to 30 min, cooled to 15° C. to about 35° C., mixed for about 30 min to 4 hrs, isolated and dried at temperature of 45° C. to 85° C. preferably at 60° C. to 70° C. gives the levofloxacin hemihydrate.

Workup

  1. additionby mixing for about 30 min to 2 hrs
  2. customRemoved the insolubles
  3. filtrationby filtration
  4. additiontreated the clear solution with carbon
  5. distillationdistilled off the toluene-chloroform at temperature below 60° C
  6. additionIsopropanol is added to the mass, temperature
  7. temperatureis raised to 65° C. to 90° C.
  8. additionis added to the reaction mass at temperature of 60° C. to 90° C.
  9. additionmixed for about 5 min to 30 min
  10. temperaturecooled to 15° C. to about 35° C.
  11. additionmixed for about 30 min to 4 hrs
  12. customisolated
  13. customdried at temperature of 45° C. to 85° C. preferably at 60° C. to 70° C.

Sources & evidence

ORD record
ord-e159a1dc868547618726dc0b2899ed0e
Source dataset
uspto-grants-2010_03
Patent number
US07678903B2

Reaction notes

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