Ethanol → HCID 68433833, compound

HRID 1018542Notes

Reaction equation

HRID 1018542 reaction equation
C(O)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.[S:35](=[O:39])(=[O:38])([OH:37])[OH:36]>O>[S:35]([OH:39])([OH:38])(=[O:37])=[O:36].[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 1118Sulfuric AcidHCID 124093Garenoxacin

Product 1

HCID 68433833HCID 68433833, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

In 10 ml of 50% water-containing ethanol is suspended 0.5 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 then warmed to 50° C., after which 0.12 g of sulfuric acid is added thereto to form a uniform solution. Subsequently, the solution is stirred at the same temperature for 10 minutes and then filtered. The filtrate is cooled to room temperature and thereafter the crystals deposited are collected by filtration to obtain 0.34 g of (R)-1-cyclopropyl-8-difluoromethoxy-7-(1-methyl-2,3-dihydro-1H-5-isoindolyl)-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid sulfate.

Workup

  1. customto form a uniform solution
  2. filtrationfiltered
  3. temperatureThe filtrate is cooled to room temperature
  4. filtrationthe crystals deposited are collected by filtration

Sources & evidence

ORD record
ord-750b023080a4441b9560a408e230d34c
Source dataset
uspto-grants-2002_11
Patent number
US06482835B2

Reaction notes

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