Hydrochloric Acid → HCID 19072271, compound

HRID 1955760Notes

Reaction equation

HRID 1955760 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH:9]1([N:12]2[C:21]3[C:16](=[CH:17][C:18]([F:42])=[C:19]([C:24]([C:26]([O:28][CH:29]([C:36]4[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=4)[C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])=[CH2:25])[C:20]=3[O:22][CH3:23])[C:15](=[O:43])[C:14]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:13]2)[CH2:11][CH2:10]1.Cl>CN(C)C=O.O.C(OCC)(=O)C>[CH:9]1([N:12]2[C:21]3[C:16](=[CH:17][C:18]([F:42])=[C:19]([C:24]4([C:26]([O:28][CH:29]([C:30]5[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=5)[C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)=[O:27])[CH2:4][CH2:25]4)[C:20]=3[O:22][CH3:23])[C:15](=[O:43])[C:14]([C:44]([O:46][CH2:47][CH3:48])=[O:45])=[CH:13]2)[CH2:10][CH2:11]1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 19072254HCID 19072254, compound

Product 1

HCID 19072271HCID 19072271, compoundYield 26.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

160 mg of 60% sodium hydride was suspended in 18 ml of N,N-dimethylformamide and 877 mg of trimethylsulfoxonium iodide was added thereto under ice-cooling. After stirring at room temperature for 40 minutes, 1.80 g of ethyl 1-cyclopropyl-7-(l-diphenylmethoxycarbonylvinyl)-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate was added thereto and the resulting mixture was stirred at 50° C. for 3 hours. To the reaction mixture, 30 ml of ethyl acetate and 15 ml of water were added and the pH value of the mixture was regulated to 1 with 2N hydrochloric acid. Then the organic layer was collected, successively washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, the residue thus obtained was crystallized by adding ethyl acetate/n-hexane and the crystals were collected by filtration. Thus 497 mg of ethyl 1-cyclopropyl-7-(1-diphenylmethoxycarbonylcyclopropyl)-6- fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quinolinecarboxylate was obtained (yield: 26.9%).

Workup

  1. temperatureunder ice-cooling
  2. stirringthe resulting mixture was stirred at 50° C. for 3 hours
  3. customThen the organic layer was collected
  4. washsuccessively washed with water
  5. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate
  6. customAfter removing the solvent under reduced pressure
  7. customthe residue thus obtained
  8. customwas crystallized
  9. additionby adding ethyl acetate/n-hexane
  10. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-f322f6abff3f41a1b7ebd6e7753e1acc
Source dataset
uspto-grants-1998_07
Patent number
US05776948

Reaction notes

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