Hydrochloric Acid → HCID 19072264, compound

HRID 1955761Notes

Reaction equation

HRID 1955761 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:33])=[C:11]([CH2:16][C:17]([O:19][CH:20]([C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:18])[C:12]=3[O:14][CH3:15])[C:7](=[O:34])[C:6]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:5]2)[CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:43][CH2:44][CH2:45][CH2:46]Br.Cl>CN(C)C=O.O.C(OCC)C.C(OCC)(=O)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:33])=[C:11]([C:16]4([C:17]([O:19][CH:20]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)=[O:18])[CH2:46][CH2:45][CH2:44][CH2:43]4)[C:12]=3[O:14][CH3:15])[C:7](=[O:34])[C:6]([C:35]([O:37][CH2:38][CH3:39])=[O:36])=[CH:5]2)[CH2:2][CH2:3]1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 80561,4-DibromobutaneHCID 24758Sodium hydrideHCID 19072265HCID 19072265, compound

Product 1

HCID 19072264HCID 19072264, compoundYield 79.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

10 g of ethyl 1-cyclopropyl-7-diphenylmethoxycar-bonylmethyl-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quino-linecarboxylate was dissolved in 300 ml of N,N-dimethylform-amide and 1.89 g of 60% sodium hydride was added thereto under ice-cooling. After stirring for 45 minutes, 5.43 g of 1,4-dibromobutane was added thereto and the resulting mixture was stirred at room temperature for 20 hours. After regulating the pH value of the mixture to 5 with 2N hydro-chloric acid, 100 ml of ethyl acetate, 100 ml of diethyl ether and 100 ml of water were added thereto. Then the organic layer was collected, successively washed with water and a saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous sodium sulfate. After removing the solvent under reduced pressure, diisopropyl ether was added to the crystalline product thus obtained followed by the collection of the product by filtration. Thus 8.72 g of ethyl 1-cyclopropyl-7-(1-diphenylmethoxycarbonylcyclo-pentyl)-6-fluoro-8-methoxy-1,4-dihydro-4-oxo-3-quino-linecarboxylate was obtained (yield: 79.1%).

Workup

  1. temperatureunder ice-cooling
  2. stirringthe resulting mixture was stirred at room temperature for 20 hours
  3. additionwere added
  4. customThen the organic layer was collected
  5. washsuccessively washed with water
  6. dry with materiala saturated aqueous solution of sodium hydrogencarbonate and dried over anhydrous sodium sulfate
  7. customAfter removing the solvent under reduced pressure, diisopropyl ether
  8. additionwas added to the crystalline product
  9. customthus obtained
  10. filtrationfollowed by the collection of the product by filtration

Sources & evidence

ORD record
ord-12d620289ed94237a18a36a531ec2aa2
Source dataset
uspto-grants-1998_07
Patent number
US05776948

Reaction notes

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