Trifluoroacetic acid → HCID 21474803, compound

HRID 1901740Notes

Reaction equation

HRID 1901740 reaction equation
FC(F)(F)C(O)=O.[O:8]=[C:9]([CH2:45][CH3:46])[CH2:10][O:11][C:12]1[CH:44]=[CH:43][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[N:19](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:18]2=[O:42])=[CH:14][CH:13]=1>C(Cl)Cl>[O:8]=[C:9]([CH2:45][CH3:46])[CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][CH:17]2[S:21][C:20](=[O:22])[NH:19][C:18]2=[O:42])=[CH:43][CH:44]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21474776HCID 21474776, compound

Product 1

HCID 21474803HCID 21474803, compoundYield 90.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

50 ml of trifluoroacetic acid were added to a solution of 19.3 g of 5-[4-(2-oxobutoxy)benzyl]-3-triphenylmethylthiazolidine-2,4-dione (prepared as described in Preparation 94) in 100 ml of methylene chloride, and the mixture was stirred at room temperature for 1.5 hours. At the end of this time, it was concentrated by evaporation under reduced pressure. Water was added to the residue, and the mixture was neutralized with sodium hydrogencarbonate and then extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed by evaporation under reduced pressure, and the resulting residue was applied to a silica gel chromatography column, and eluted, using a 1:2 by volume mixture of ethyl acetate and hexane as the eluent. It was then recrystallized from a mixture of ethyl acetate and diisopropyl ether, to give 9.55 g of the title compound, melting at 141.5° to 145.7° C.

Workup

  1. concentrationAt the end of this time, it was concentrated by evaporation under reduced pressure
  2. additionWater was added to the residue
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with an aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe ethyl acetate was removed by evaporation under reduced pressure
  7. washeluted
  8. additionby volume mixture of ethyl acetate and hexane as the eluent
  9. customIt was then recrystallized from a mixture of ethyl acetate and diisopropyl ether

Sources & evidence

ORD record
ord-89aac7d69dc34c218ede139174aa77ab
Source dataset
uspto-grants-1996_11
Patent number
US05578620

Reaction notes

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