Ethanol → Garenoxacin Mesylate

HRID 1250359Notes

Reaction equation

HRID 1250359 reaction equation
C([OH:3])C.[CH:4]1([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[C@@H:26]([CH3:30])[NH:25][CH2:24]5)[C:15]=3[O:17][CH:18]([F:20])[F:19])[C:10](=[O:31])[C:9]([C:32]([OH:34])=[O:33])=[CH:8]2)[CH2:6][CH2:5]1.[CH3:35][S:36]([OH:39])(=[O:38])=[O:37]>O>[OH2:3].[CH3:35][S:36]([OH:39])(=[O:38])=[O:37].[CH:4]1([N:7]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:21]4[CH:22]=[C:23]5[C:27](=[CH:28][CH:29]=4)[C@@H:26]([CH3:30])[NH:25][CH2:24]5)[C:15]=3[O:17][CH:18]([F:20])[F:19])[C:10](=[O:31])[C:9]([C:32]([OH:34])=[O:33])=[CH:8]2)[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 702EthanolHCID 6395Methanesulfonic AcidHCID 124093Garenoxacin

Product 1

HCID 157690Garenoxacin Mesylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

In 192 ml of 50% water-containing ethanol is suspended 24 g of (R)-1-cyclopropyl-8-difluoromethoxy-7-(1-methyl-2,3-dihydro-1H-5-isoindolyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid and the suspension is warmed to 40° C., after which 5.71 g of methanesulfonic acid is added to the warmed suspension to form a uniform solution. Subsequently, the solution is stirred at the same temperature for 10 minutes and thereafter filtered, and the filtrate is concentrated, after which the crystals deposited are collected by filtration to obtain 26.64 g of (R)-1-cyclopropyl-8-difluoromethoxy-7-(1-methyl-2,3-dihydro-1H-5-isoindolyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid methanesulfonate monohydrate.

Workup

  1. customto form a uniform solution
  2. filtrationfiltered
  3. concentrationthe filtrate is concentrated
  4. filtrationafter which the crystals deposited are collected by filtration

Sources & evidence

ORD record
ord-0da226f37f284778b75948747e782774
Source dataset
uspto-grants-2002_01
Patent number
US06337399B1

Reaction notes

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