Methanesulfonic Acid → HCID 178505301, compound

HRID 636543Notes

Reaction equation

HRID 636543 reaction equation
[CH3:1][C@H:2]([NH2:40])[C:3]([NH:5][C@H:6]([C:8]([NH:10][C@@H:11]1[C@H:13]2[CH2:14][N:15]([C:17]3[N:22]=[C:21]4[N:23]([C:31]5[CH:32]=[CH:33][C:34]([F:38])=[CH:35][C:36]=5[F:37])[CH:24]=[C:25]([C:28]([OH:30])=[O:29])[C:26](=[O:27])[C:20]4=[CH:19][C:18]=3[F:39])[CH2:16][C@@H:12]12)=[O:9])[CH3:7])=[O:4].[CH3:41][S:42]([OH:45])(=[O:44])=[O:43]>C(O)C>[CH3:1][C@H:2]([NH2:40])[C:3]([NH:5][C@H:6]([C:8]([NH:10][C@@H:11]1[C@H:13]2[CH2:14][N:15]([C:17]3[N:22]=[C:21]4[N:23]([C:31]5[CH:32]=[CH:33][C:34]([F:38])=[CH:35][C:36]=5[F:37])[CH:24]=[C:25]([C:28]([OH:30])=[O:29])[C:26](=[O:27])[C:20]4=[CH:19][C:18]=3[F:39])[CH2:16][C@@H:12]12)=[O:9])[CH3:7])=[O:4].[CH3:41][S:42]([OH:45])(=[O:44])=[O:43]

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 178462181HCID 178462181, compound

Product 1

HCID 178505301HCID 178505301, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
2.5 °C

Procedure

Alatrofloxacin zwitterion (25 g wet cake) as either a wet cake or dry product was combined with 10% aqueous ethanol (242 mL), and then methanesulfonic acid (1.9 mL) was added to the slurry to adjust the pH to about 3.5-4.5. The reaction mixture was then heated to reflux, filtered and then concentrated at atmospheric pressure to approximately one-half of its original volume. The solution was then cooled to 0-5° C., and the resulting solids were granulated for 1 hour. After the solids were filtered and washed with ethanol (39 mL), the alatrofloxacin mesylate was dried for 24 hours at 40° C. Alatrofloxacin mesylate (17.7 g), suitable for parenteral formulation, was isolated in 90% yield.

Workup

  1. temperatureThe reaction mixture was then heated
  2. temperatureto reflux
  3. filtrationfiltered
  4. concentrationconcentrated at atmospheric pressure to approximately one-half of its original volume
  5. filtrationAfter the solids were filtered
  6. washwashed with ethanol (39 mL)
  7. dry with materialthe alatrofloxacin mesylate was dried for 24 hours at 40° C

Sources & evidence

ORD record
ord-dfd2048a37ec452596d7e0b7e9c4ca8c
Source dataset
uspto-grants-2001_02
Patent number
US06194429B1

Reaction notes

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