Trifluoroacetic acid → HCID 67102076, compound

HRID 2080390Notes

Reaction equation

HRID 2080390 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.Cl.C(O)C>ClCCl>[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 3

HCID 6422Trifluoroacetic acidHCID 21887872Ethanol hydrochlorideHCID 23114547HCID 23114547, compound

Product 1

HCID 67102076HCID 67102076, compoundYield 194.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

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). Trifluoroacetic acid (5.0 ml) was added dropwise to the resulting solution under ice cooling. The reaction mixture was stirred at room temperature for 2 hours and then, concentrated under reduced pressure. To the residue thus obtained were added dichloromethane (10 ml) and a 1N hydrochloric acid-ethanol solution (10 ml). The resulting mixture was concentrated under reduced pressure to give a white solid. The resulting solid was washed with diethyl ether to give the title compound (1.36 g, 3.12 mmol, 97%) as a white powder.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customTo the residue thus obtained
  3. concentrationThe resulting mixture was concentrated under reduced pressure
  4. customto give a white solid
  5. washThe resulting solid was washed with diethyl ether

Sources & evidence

ORD record
ord-bcad5d9db86f44208c6999a9eb3532ee
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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