Ethyl bromoacetate → HCID 86633055, compound

HRID 1094181Notes

Reaction equation

HRID 1094181 reaction equation
[CH3:1][O:2][C:3](=[O:30])[CH:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([NH:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:12]([F:17])[CH:13]=2)[N:8]([CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:7]=1)[OH:5].[H-].[Na+].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].C(=O)([O-])O.[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:30])[CH:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][C:11]([NH:18][CH:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[C:12]([F:17])[CH:13]=2)[N:8]([CH:25]2[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:7]=1)[O:5][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetate2×HCID 24758Sodium hydride2×HCID 516892Sodium BicarbonateHCID 86633054HCID 86633054, compound

Product 1

HCID 86633055HCID 86633055, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

146 mg of methyl[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl](hydroxy)acetate was dissolved in 10 ml of THF, and 46 mg of 60% sodium hydride was added under ice-cooling, followed by stirring at room temperature for 30 minutes. Then, 58 μl of ethyl bromoacetate was added to the reaction mixture, followed by stirring at room temperature for 5 hours. 46 mg of 60% sodium hydride and 10 ml of THF were further added under ice-cooling, followed by stirring at room temperature for 2 hours. Then, 58 μl of ethyl bromoacetate was added thereto, followed by stirring at room temperature for 17 hours. Aqueous saturated sodium hydrogen carbonate was added to the reaction mixture, followed by extraction with ethyl acetate. Then, the organic layer was washed with aqueous saturated sodium chloride. After drying over anhydrous sodium sulfate, concentration was carried out under a reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain 66 mg of methyl[7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinolin-3-yl](2-ethoxy-2-oxoethoxy)acetate.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 5 hours
  3. temperaturecooling
  4. stirringby stirring at room temperature for 2 hours
  5. stirringby stirring at room temperature for 17 hours
  6. extractionfollowed by extraction with ethyl acetate
  7. washThen, the organic layer was washed with aqueous saturated sodium chloride
  8. dry with materialAfter drying over anhydrous sodium sulfate, concentration
  9. customThe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0c2f8e4746a84f1fb2e3d3e44019bfee
Source dataset
uspto-grants-2012_03
Patent number
US08133882B2

Reaction notes

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