Trifluoroacetic acid → N-[5-[(4-Chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)pentyl]methanesulfonamide

HRID 748786Notes

Reaction equation

HRID 748786 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[CH2:12][CH2:13][CH2:14][CH2:15][N:16]([S:24]([CH3:27])(=[O:26])=[O:25])C(=O)OC(C)(C)C)(=[O:10])=[O:9])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.CCCCCC.C(OCC)(=O)C.CCCCCC>ClCCl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([CH:11]([C:28]2[CH:33]=[C:32]([F:34])[CH:31]=[CH:30][C:29]=2[F:35])[CH2:12][CH2:13][CH2:14][CH2:15][NH:16][S:24]([CH3:27])(=[O:26])=[O:25])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8058HexaneHCID 21226206Ethyl acetate hexaneHCID 59750747t-butyl N-[5-[(4-Chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)pentyl]-N-methylsulfonylcarbamate

Product 1

HCID 59750815N-[5-[(4-Chlorophenyl)sulfonyl]-5-(2,5-difluorophenyl)pentyl]methanesulfonamideYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In dichloromethane (4 ml) was dissolved t-butyl N-[5-[(4-chlorophenyl)sulfonyl]-5(2,5-difluorophenyl)pentyl]-N-methylsulfonylcarbamate (108 mg, 0.196 mmol), followed by the addition of trifluoroacetic acid (1 ml) at room temperature. The resulting mixture was stirred at room temperature for 3 hours. The reaction mixture was diluted with dichloromethane, washed successively with water, a saturated aqueous solution of sodium bicarbonate, and brine, dried over magnesium sulfate and then concentrated. The residue thus obtained was subjected to flash chromatography on a silica gel column, and the fraction obtained from the hexane:ethyl acetate=1:1 eluate was concentrated, whereby the solid thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (75.5 mg, 0.167 mmol, 85%) was obtained as a white powder.

Workup

  1. washwashed successively with water
  2. dry with materiala saturated aqueous solution of sodium bicarbonate, and brine, dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue thus obtained
  5. concentrationethyl acetate=1:1 eluate was concentrated
  6. customwhereby the solid thus obtained

Sources & evidence

ORD record
ord-0072b5a536484dd9b82f2fc26fa9abc3
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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