Methanesulfonic Acid → 1433857-41-0

HRID 520803Notes

Reaction equation

HRID 520803 reaction equation
[CH:1]1([NH:4][CH2:5][C@@H:6]2[C@H:10]([F:11])[CH2:9][N:8]([C:12]3[C:21]([O:22][CH3:23])=[C:20]4[C:15]([C:16](=[O:30])[C:17]([C:27]([OH:29])=[O:28])=[CH:18][N:19]4[CH2:24][CH2:25][F:26])=[CH:14][C:13]=3[F:31])[CH2:7]2)[CH2:3][CH2:2]1.[CH3:32][S:33]([OH:36])(=[O:35])=[O:34]>CC(C)=O>[CH3:32][S:33]([OH:36])(=[O:35])=[O:34].[CH:1]1([NH:4][CH2:5][C@@H:6]2[C@H:10]([F:11])[CH2:9][N:8]([C:12]3[C:21]([O:22][CH3:23])=[C:20]4[C:15]([C:16](=[O:30])[C:17]([C:27]([OH:29])=[O:28])=[CH:18][N:19]4[CH2:24][CH2:25][F:26])=[CH:14][C:13]=3[F:31])[CH2:7]2)[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 71528768Lascufloxacin

Product 1

HCID 715699481433857-41-0Yield 91.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Conditions

Temperature
40 °C

Procedure

3.36 L of acetone was added to 178 g of 7-{(3S,4S)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidine-1-yl}-6-fluoro-1-(2-fluoroethyl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid synthesized according to Reference Example 3, and the mixture was heated for dissolution. 0.48 L of an acetone solution of 59.1 g of methanesulfonic acid was added dropwise to the solution at an internal temperature of around 40° C. (the solution obtained is hereinafter referred to as a solution mixture). The solution mixture was stirred at an internal temperature of around 40° C. for 0.5 hours. The solution mixture was cooled and stirred at an internal temperature of 10° C. or less for 0.5 hours. Precipitated crystals were separated by filtration, washed with 1.44 L of acetone, and dried at 50° C. under reduced pressure for 2 hours to obtain 198 g of crude 7-{(3S,4S)-3-[(cyclopropylamino)methyl]-4-fluoropyrrolidine-1-yl}-6-fluoro-1-(2-fluoroethyl)-8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid methanesulfonate salt.

Workup

  1. customsynthesized
  2. temperaturethe mixture was heated for dissolution
  3. customobtained
  4. temperatureThe solution mixture was cooled
  5. stirringstirred at an internal temperature of 10° C. or less for 0.5 hours
  6. customPrecipitated crystals
  7. customwere separated by filtration
  8. washwashed with 1.44 L of acetone
  9. customdried at 50° C. under reduced pressure for 2 hours

Sources & evidence

ORD record
ord-f5cf721cf09449b0b9085402a421ea14
Source dataset
uspto-grants-2016_05
Patent number
US09328089B2

Reaction notes

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