Sodium Bicarbonate → HCID 178511751, compound

HRID 1108260Notes

Reaction equation

HRID 1108260 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 (prepared according to Example 13B of the '402 patent) (20 g) was stirred with demineralized water (100 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. The crystals were isolated by filtration and washed with demineralized water (27 mL). The wet crystals were suspended in demineralized water (100 mL) and stirred for about 1 hour at about 50° C., then cooled to about 20° C. and stirred at this temperature for about 1 hour. The crystals were filtered from the mother liquor, washed with demineralized water (about 27 mL) and dried to constant weight under vacuum at about 40° C. to yield the title product which contained 2.5% residual water by analysis. Yield 16.25 g, 97%.

Workup

  1. temperatureto cool to about 25° C.
  2. customThe crystals were isolated by filtration
  3. washwashed with demineralized water (27 mL)
  4. stirringstirred for about 1 hour at about 50° C.
  5. temperaturecooled to about 20° C.
  6. stirringstirred at this temperature for about 1 hour
  7. filtrationThe crystals were filtered from the mother liquor
  8. washwashed with demineralized water (about 27 mL)
  9. customdried to constant weight under vacuum at about 40° C.

Sources & evidence

ORD record
ord-89734773484b4c23941bf3f7769aaa99
Source dataset
uspto-grants-2000_05
Patent number
US06066647

Reaction notes

Loading…