Hydrochloric Acid → Ethyl 1,4-dihydro-8-fluoro-6-iodo-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-oxo-3-quinolinecarboxylate

HRID 491522Notes

Reaction equation

HRID 491522 reaction equation
F[C:2]1[C:27]([F:28])=[CH:26][C:25]([I:29])=[CH:24][C:3]=1[C:4]([C:6](=[CH:12][NH:13][CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])[C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5].[H-].[Na+].Cl.O>C1COCC1>[F:28][C:27]1[CH:26]=[C:25]([I:29])[CH:24]=[C:3]2[C:2]=1[N:13]([CH2:14][CH2:15][O:16][Si:17]([C:20]([CH3:21])([CH3:22])[CH3:23])([CH3:19])[CH3:18])[CH:12]=[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:4]2=[O:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 24758Sodium hydrideHCID 178472040HCID 178472040, compound

Product 1

HCID 23083974Ethyl 1,4-dihydro-8-fluoro-6-iodo-1-[2-(tert-butyldimethylsilyloxy)ethyl]-4-oxo-3-quinolinecarboxylateYield 92%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Ethyl 2-(2,3-difluoro-5-iodobenzoyl)-3-[2-(tert-butyldimethylsilyloxy)ethylamino]acrylate (2.3 g, 4.3 mmol) obtained in Step 3 was dissolved in THF (25 ml), sodium hydride (256 mg, 6.4 mmol) was added under ice-cooling and the mixture was stirred at 0° C. for 1 hr. 1N Hydrochloric acid (6.4 ml, 6.4 mmol) was added to neutralize the reaction mixture. Water was further added and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried over sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=1:2 to ethyl acetate:hexane=2:1) to give the object product (2.0 g, yield 92%) as a white solid.

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=1:2 to ethyl acetate:hexane=2:1)

Sources & evidence

ORD record
ord-52e0a1b389724202bd1b485b08524b62
Source dataset
uspto-grants-2009_05
Patent number
US07531554B2

Reaction notes

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