Sulfuric Acid → HCID 86633054, compound

HRID 469221Notes

Reaction equation

HRID 469221 reaction equation
[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:28])[C:13]([CH:23]([OH:27])[C:24]([OH:26])=[O:25])=[CH:14][N:15]3[CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:10][C:9]=2[F:29])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.[C:35](=O)([O-])O.[Na+]>CO>[CH:1]1([NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12](=[O:28])[C:13]([CH:23]([OH:27])[C:24]([O:26][CH3:35])=[O:25])=[CH:14][N:15]3[CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)=[CH:10][C:9]=2[F:29])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 66636889HCID 66636889, compound

Product 1

HCID 86633054HCID 86633054, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

52 mg of [7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl](hydroxy)acetic acid was dissolved in 10 ml of methanol, and 0.4 ml of concentrated sulfuric acid was added, followed by stirring at room temperature for 1 hour. Aqueous saturated sodium hydrogen carbonate was added to the reaction mixture, followed by extraction with ethyl acetate, washing with aqueous saturated sodium chloride and concentration under a reduced pressure. The resulting residue was recrystallized from aqueous methanol to obtain 53 mg of methyl [7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl](hydroxy)acetate.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washwashing with aqueous saturated sodium chloride and concentration under a reduced pressure
  3. customThe resulting residue was recrystallized from aqueous methanol

Sources & evidence

ORD record
ord-9eac61ac257e4cebbc4ca060678fc303
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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