Sodium Bicarbonate → HCID 178511751, compound

HRID 1108261Notes

Reaction equation

HRID 1108261 reaction equation
CS(O)(=O)=O.[CH:6]1[C:11]([F:12])=[CH:10][C:9]([F:13])=[C:8]([N:14]2[C:20]3=[N:21][C:22]([N:26]4[CH2:30][C@@H:29]5[C@@H:31]([NH2:32])[C@@H:28]5[CH2:27]4)=[C:23]([F:25])[CH:24]=[C:19]3[C:17](=[O:18])[C:16]([C:33]([OH:35])=[O:34])=[CH:15]2)[CH:7]=1.C(=O)(O)[O-].[Na+]>O>[CH:6]1[C:11]([F:12])=[CH:10][C:9]([F:13])=[C:8]([N:14]2[C:20]3=[N:21][C:22]([N:26]4[CH2:30][C@@H:29]5[C@@H:31]([NH2:32])[C@@H:28]5[CH2:27]4)=[C:23]([F:25])[CH:24]=[C:19]3[C:17](=[O:18])[C:16]([C:33]([OH:35])=[O:34])=[CH:15]2)[CH:7]=1

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 178505347HCID 178505347, compound

Product 1

HCID 178511751HCID 178511751, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Trovafloxacin mesylate, (75 g) was stirred with demineralised water (375 mL). The crystal slurry was heated to about 50° C. and the slurry adjusted to a pH of about 8.0 by addition of saturated sodium bicarbonate solution. The slurry was held at about 50° C. for 30 minutes, allowed to cool to about 25° C. and stirred at this temperature for 30 minutes. Crystals were isolated by filtration and washed with demineralised water (100 mL). The wet crystals were suspended in demineralised water (375 mL) and stirred for 1 hour at about 50° C., then cooled to about 20° C. and stirred at this temperature for about 1 hour. The crystalline product was filtered from the mother liquor and washed with demineralised water (about 100 mL). The wet crystals were stirred with ethyl acetate (1125 mL) and the resultant slurry heated to reflux and the water azeotropically removed. The essentially anhydrous slurry was cooled to about 25° C., the crystals were isolated by filtration and dried under vacuum at 40° C. until all the solvent had been removed to provide the title product. Yield 60.9 g, 94%.

Workup

  1. temperatureto cool to about 25° C.
  2. customCrystals were isolated by filtration
  3. washwashed with demineralised water (100 mL)
  4. stirringstirred for 1 hour at about 50° C.
  5. temperaturecooled to about 20° C.
  6. stirringstirred at this temperature for about 1 hour
  7. filtrationThe crystalline product was filtered from the mother liquor
  8. washwashed with demineralised water (about 100 mL)
  9. stirringThe wet crystals were stirred with ethyl acetate (1125 mL)
  10. temperaturethe resultant slurry heated
  11. temperatureto reflux
  12. customthe water azeotropically removed
  13. temperatureThe essentially anhydrous slurry was cooled to about 25° C.
  14. customthe crystals were isolated by filtration
  15. customdried under vacuum at 40° C. until all the solvent
  16. customhad been removed

Sources & evidence

ORD record
ord-0a17eead27dc4b5d89469ccbec352d0a
Source dataset
uspto-grants-2000_05
Patent number
US06066647

Reaction notes

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