Citric Acid → HCID 23284721, compound

HRID 369331Notes

Reaction equation

HRID 369331 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([F:40])=[CH:11][C:12]([F:39])=[C:13]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:32])=[C:22]([F:31])[C:23]=3[C:25]#[C:26][Si](C)(C)C)[C:18](=[O:33])[C:17]([C:34]([O:36]CC)=[O:35])=[CH:16]2)[CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C:9]1[C:10]([F:40])=[CH:11][C:12]([F:39])=[C:13]([N:15]2[C:24]3[C:19](=[CH:20][C:21]([F:32])=[C:22]([F:31])[C:23]=3[C:25]#[CH:26])[C:18](=[O:33])[C:17]([C:34]([OH:36])=[O:35])=[CH:16]2)[CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 14798Sodium HydroxideHCID 23284663HCID 23284663, compound

Product 1

HCID 23284721HCID 23284721, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-(5-tert-butoxycarbonylamino-2,4-difluorophenyl)-6,7-difluoro-8-(trimethylsilylethynyl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (750 mg) was dissolved in tetrahydrofuran (6 ml). 1N Sodium hydroxide (2 ml) was added to this solution, and the mixture was stirred overnight at room temperature. After the reaction mixture was acidified with citric acid and then extracted with chloroform. An organic layer was dried over anhydrous magnesium sulfate, and the solvent was then distilled off under reduced pressure to obtain the title compound (240 mg) as a colorless powder.

Workup

  1. extractionextracted with chloroform
  2. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was then distilled off under reduced pressure

Sources & evidence

ORD record
ord-8103cb588a454062ad77dd6ae67480ca
Source dataset
uspto-grants-2000_10
Patent number
US06136823

Reaction notes

Loading…