Trifluoroacetic acid → HCID 67102076, compound

HRID 748825Notes

Reaction equation

HRID 748825 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])[CH:12]2[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O>ClCCl.C(OCC)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:25]2[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:26]=2[F:32])[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 23114547HCID 23114547, compound

Product 1

HCID 67102076HCID 67102076, compoundYield 194.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

In dichloromethane (50 ml) was dissolved t-butyl 4-[[(4-chlorophenyl)sulfonyl](2,5-difluorophenyl)methyl]-1-piperidinecarboxylate (1.56 g, 3.21 mmol). Under ice cooling, trifluoroacetic acid (5.0 ml) was added dropwise to the resulting solution. After stirring at room temperature for 2 hours, the reaction mixture was concentrated under reduced pressure. Dichloromethane (10 ml) and a 1N ethanol solution (10 ml) of hydrochloric acid were added, followed by concentration under reduced pressure to give a white solid. The resulting solid was washed with diethyl ether, whereby the title compound (1.36 g, 3.12 mmol, 97%) was obtained as a white powder.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionDichloromethane (10 ml) and a 1N ethanol solution (10 ml) of hydrochloric acid were added
  3. concentrationfollowed by concentration under reduced pressure
  4. customto give a white solid

Sources & evidence

ORD record
ord-67944e372ba34e6ba6ffa2f717f58eee
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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