Hydrochloric Acid → 6-[(3-Chloro-2-fluorophenyl)methyl]-7-fluoro-1-[(2S)-1-hydroxy-3-methylbutan-2-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 1670797Notes

Reaction equation

HRID 1670797 reaction equation
[Cl:1][C:2]1[C:3]([F:36])=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[F:16])[N:12]([C@@H:17]([CH:24]([CH3:26])[CH3:25])[CH2:18][O:19]C(OC)=O)[CH:11]=[C:10]([C:27]([O:29]CC)=[O:28])[C:9]2=[O:32].[OH-].[Na+].Cl>CC(O)C>[Cl:1][C:2]1[C:3]([F:36])=[C:4]([CH:33]=[CH:34][CH:35]=1)[CH2:5][C:6]1[CH:7]=[C:8]2[C:13](=[CH:14][C:15]=1[F:16])[N:12]([C@@H:17]([CH:24]([CH3:26])[CH3:25])[CH2:18][OH:19])[CH:11]=[C:10]([C:27]([OH:29])=[O:28])[C:9]2=[O:32]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 58801741HCID 58801741, compound

Product 1

HCID 588017116-[(3-Chloro-2-fluorophenyl)methyl]-7-fluoro-1-[(2S)-1-hydroxy-3-methylbutan-2-yl]-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of 19 (270 mg, 0.52 mmol) in 2-propanol (5 mL) was added 4N sodium hydroxide (1 mL) and the solution was stirred at rt for 3 h. The reaction mixture was acidified with 2N HCl (10 mL) and extracted with EtOAc (15 mL). The phases were separated and the aqueous phase was extracted with EtOAc (15 mL). The combined organic solution was dried over Na2SO4, filtered and concentrated under reduced pressure to give 220 mg (95%, 98% purity) of 20 as a white solid.

Workup

  1. extractionextracted with EtOAc (15 mL)
  2. customThe phases were separated
  3. extractionthe aqueous phase was extracted with EtOAc (15 mL)
  4. dry with materialThe combined organic solution was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bf7f3accc2eb4284aef5e413421cc283
Source dataset
uspto-grants-2011_08
Patent number
US07994194B2

Reaction notes

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