Sodium Hydroxide → HCID 69960324, compound

HRID 1584832Notes

Reaction equation

HRID 1584832 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:33])=[C:11]([C:16]4[CH:17]=[C:18]5[C:24](=[CH:25][CH:26]=4)[C:21]4([CH2:23][CH2:22]4)[N:20](C(=O)C(F)(F)F)[CH2:19]5)[C:12]=3[O:14][CH3:15])[C:7](=[O:34])[C:6]([C:35]([O:37]CC)=[O:36])=[CH:5]2)[CH2:3][CH2:2]1.[OH-].[Na+].O1CCOCC1>C(O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:33])=[C:11]([C:16]4[CH:17]=[C:18]5[C:24](=[CH:25][CH:26]=4)[C:21]4([CH2:22][CH2:23]4)[NH:20][CH2:19]5)[C:12]=3[O:14][CH3:15])[C:7](=[O:34])[C:6]([C:35]([OH:37])=[O:36])=[CH:5]2)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 21220249HCID 21220249, compound

Product 1

HCID 69960324HCID 69960324, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

To a suspension of 210 mg of ethyl 1-cyclopropyl-6-fluoro-8-methoxy-7-[2-trifluoroacetyl-spiro[isoindolin-1,1'-cyclopropan]-5-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylate in 4.2 ml of ethanol were added 2.1 ml of 1N aqueous sodium hydroxide solution and 4.2 ml of dioxane, after which the resulting mixture was heated with stirring at 40° C. for three hours. The reaction mixture was cooled to room temperature, and thereafter, insolubles were removed by filtration, after which a carbon dioxide gas was blown in the filtrate obtained. The crystals precipitated were collected by filtration, to obtain 140 mg of pale yellow, crystalline 1-cyclopropyl-6-fluoro-8-methoxy-7-[spiro[isoindolin-1,1'-cyclopropan]-5-yl]-1,4-dihydro-4-oxoquinoline-3-carboxylic acid.

Workup

  1. temperatureafter which the resulting mixture was heated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. custominsolubles were removed by filtration
  4. customobtained
  5. customThe crystals precipitated
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-fa5c5bacc99247608144e26e1b799c6d
Source dataset
uspto-grants-1999_08
Patent number
US05935952

Reaction notes

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