Trifluoroacetic acid → 3-((2-((7-Chloro-6-fluoro-2-quinolinyl)methoxy)-6,11-dihydrodibenz(b,E)oxepin-11-yl)thio)propanoic acid, (+)-

HRID 232827Notes

Reaction equation

HRID 232827 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:29]=[CH:28][C:17]4[O:18][CH2:19][C:20]5[CH:27]=[CH:26][CH:25]=[CH:24][C:21]=5[CH:22](O)[C:16]=4[CH:15]=3)=[N:9]2)=[CH:4][C:3]=1[F:30].FC(F)(F)C(O)=O.[SH:38][CH2:39][CH2:40][C:41]([OH:43])=[O:42].[OH-].[Na+]>C(Cl)Cl>[C:41]([CH2:40][CH2:39][S:38][CH:22]1[C:21]2[CH:24]=[CH:25][CH:26]=[CH:27][C:20]=2[CH2:19][O:18][C:17]2[CH:28]=[CH:29][C:14]([O:13][CH2:12][C:8]3[CH:7]=[CH:6][C:5]4[C:10](=[CH:11][C:2]([Cl:1])=[C:3]([F:30])[CH:4]=4)[N:9]=3)=[CH:15][C:16]1=2)([OH:43])=[O:42]

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 65143-Mercaptopropionic AcidHCID 14798Sodium HydroxideHCID 233591342-(7-Chloro-6-fluoroquinolin-2-yl)methoxy-11-hydroxy-6,11-dihydrodibenz[b,e]oxepine

Product 1

HCID 98492103-((2-((7-Chloro-6-fluoro-2-quinolinyl)methoxy)-6,11-dihydrodibenz(b,E)oxepin-11-yl)thio)propanoic acid, (+)-Yield 52.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

While stirring under ice cooling, 1 g of 2-(7-chloro-6-fluoroquinolin-2-yl)methoxy-11-hydroxy-6,11-dihydrodibenz[b,e]oxepine was added to a mixed solution of 8 ml of trifluoroacetic acid and 6 ml of methylene chloride, then 0.25 g of 3-mercaptopropionic acid was added to the solution and the mixture was stirred under ice cooling for 2 hours. After completion of the reaction, 180 ml of ice water was added the mixture, the mixture was adjusted to about pH 3 with a 1N-sodium hydroxide aqueous solution and then the aqueous layer was extracted with 200 ml of methylene chloride. The organic layer was washed with water and dried over anhydrous sodium sulfate and the residue obtained by removing the solvent under reduced pressure was recrystallized from ethyl acetate to obtain 0.63 g of the title compound as white powder.

Workup

  1. stirringthe mixture was stirred under ice cooling for 2 hours
  2. additionwas added the mixture
  3. extractionthe aqueous layer was extracted with 200 ml of methylene chloride
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe residue obtained
  7. customby removing the solvent under reduced pressure
  8. customwas recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-809e2ba3351b4b1e86813c9d52a6b680
Source dataset
uspto-grants-1997_01
Patent number
US05591752

Reaction notes

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