Benzyl Alcohol → HCID 66636983, compound

HRID 469205Notes

Reaction equation

HRID 469205 reaction equation
C([Li])CCC.[CH2:6]([OH:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH:14]1([NH:20][C:21]2[CH:30]=[C:29]3[C:24]([C:25](=[O:39])[C:26]([C:36]([OH:38])=[O:37])=[CH:27][N:28]3[CH:31]3[CH2:35][CH2:34][CH2:33][CH2:32]3)=[C:23](F)[C:22]=2[F:41])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1.Cl>C1(C)C=CC=CC=1.C1COCC1>[CH2:6]([O:13][C:23]1[C:22]([F:41])=[C:21]([NH:20][CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19]2)[CH:30]=[C:29]2[C:24]=1[C:25](=[O:39])[C:26]([C:36]([OH:38])=[O:37])=[CH:27][N:28]2[CH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 313Hydrochloric AcidHCID 66637099HCID 66637099, compoundHCID 178418339Butyllithium

Product 1

HCID 66636983HCID 66636983, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, 3.2 ml of n-butyl lithium (1.60 M hexane solution) was added to a 2.4 ml THF solution of 0.58 ml benzyl alcohol, followed by stirring for 1 hour. The solvent was evaporated under a reduced pressure, followed by the addition of 8.0 ml of toluene for suspension. The suspension prepared was added to a toluene suspension of 400 mg of 7-(cyclohexylamino)-1-cyclopentyl-5,6-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid, which was prepared in a separate container, followed by stirring at room temperature for 6 hours. Then, 1 M hydrochloric acid was added to the reaction mixture, followed by extraction with chloroform and washing with aqueous saturated sodium chloride. After drying over anhydrous sodium sulfate and subsequent filtration, the solvent was evaporated under a reduced pressure. By recrystallizing the resulting residue using ethyl acetate, 400 mg of 5-(benzyloxy)-7-(cyclohexylamino)-1-cyclopentyl-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid was obtained.

Workup

  1. temperatureUnder ice-cooling
  2. customThe solvent was evaporated under a reduced pressure
  3. additionfollowed by the addition of 8.0 ml of toluene for suspension
  4. customThe suspension prepared
  5. customwas prepared in a separate container
  6. stirringby stirring at room temperature for 6 hours
  7. extractionfollowed by extraction with chloroform
  8. washwashing with aqueous saturated sodium chloride
  9. dry with materialAfter drying over anhydrous sodium sulfate and subsequent filtration
  10. customthe solvent was evaporated under a reduced pressure
  11. customBy recrystallizing the resulting residue

Sources & evidence

ORD record
ord-d35c175312ae4c63a18e6634366f8cea
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Reaction notes

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