Potassium Carbonate → HCID 59846210, compound

HRID 1697099Notes

Reaction equation

HRID 1697099 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6](=[O:33])[C:7]([N:9]([C:16]1[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=1[C:23](=[O:32])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]([C:7]1[N:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:16]2[C:17]([C:23](=[O:32])[C:24]=1[CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[CH:18][CH:19]=[C:20]([F:22])[CH:21]=2)=[O:33]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 66815747HCID 66815747, compound

Product 1

HCID 59846210HCID 59846210, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[5-fluoro-2-(3-phenyl-propionyl)-phenyl]-N-phenyl-oxalamic acid 2-methoxy-ethyl ester (500 mg) in MeOH (10 mL) was added K2CO3 (˜150 mg), and the reaction mixture heated at reflux under N2 for 1.5 h. The mixture was then cooled, the salts filtered, and solvent evaporated in vacuo. The residue was chromatographed (0-20% MeOH/DCM) to provide 3-benzyl-7-fluoro-4-oxo-1-phenyl-1,4-dihydro-quinoline-2-carboxylic acid 2-methoxy-ethyl ester (Compound 130). M+H=432; mp=168.0-169.0° C.

Workup

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux under N2 for 1.5 h
  3. temperatureThe mixture was then cooled
  4. filtrationthe salts filtered
  5. customsolvent evaporated in vacuo
  6. customThe residue was chromatographed (0-20% MeOH/DCM)

Sources & evidence

ORD record
ord-4484fdca495a44a9be16a5bcffec0c35
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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