Trifluoroacetic acid → N-[4-[(4-Chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methylbutyl]methanesulfonamide

HRID 748788Notes

Reaction equation

HRID 748788 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])[CH:12]([CH3:27])[CH2:13][CH2:14][N:15]([S:23]([CH3:26])(=[O:25])=[O:24])C(=O)OC(C)(C)C)(=[O:10])=[O:9])=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.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])[CH:12]([CH3:27])[CH2:13][CH2:14][NH:15][S:23]([CH3:26])(=[O:25])=[O:24])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 21226206Ethyl acetate hexaneHCID 59750918t-Butyl N-[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methylbutyl]-N-methylsulfonylcarbamate

Product 1

HCID 9955499N-[4-[(4-Chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methylbutyl]methanesulfonamideYield 89.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The t-butyl N-[4-[(4-chlorophenyl)sulfonyl]-4-(2,5-difluorophenyl)-3-methylbutyl]-N-methylsulfonylcarbamate (136 mg, 0.246 mmol) obtained in Example 243 was dissolved in dichloromethane (4 ml), followed by the addition of trifluoroacetic acid (1 ml) at room temperature. After stirring at room temperature for 6 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 solid thus obtained was recrystallized from ethyl acetate-hexane, whereby the title compound (99.5 mg, 0.220 mmol, 89%) was obtained as colorless needle crystals.

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 solid thus obtained

Sources & evidence

ORD record
ord-922e92dd585e428c9a799fe5e27e1b0b
Source dataset
uspto-grants-2008_07
Patent number
US07399775B2

Reaction notes

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