Benzhydrol 2-[2-[3,5-bis(trifluoromethyl)phenylsulfonamido]-4-trifluoromethylphenoxy]benzoate → SB 203347

HRID 1077974Notes

Reaction equation

HRID 1077974 reaction equation
C(O)(C1C=CC=CC=1)C1C=CC=CC=1.[F:15][C:16]([F:52])([F:51])[C:17]1[CH:18]=[C:19]([S:27]([NH:30][C:31]2[CH:46]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:44]=[CH:43][C:32]=2[O:33][C:34]2[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=2[C:36]([O-:38])=[O:37])(=[O:29])=[O:28])[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:22]=1>C(OCC)(=O)C.[Pd]>[F:51][C:16]([F:15])([F:52])[C:17]1[CH:18]=[C:19]([S:27]([NH:30][C:31]2[CH:46]=[C:45]([C:47]([F:50])([F:49])[F:48])[CH:44]=[CH:43][C:32]=2[O:33][C:34]2[CH:42]=[CH:41][CH:40]=[CH:39][C:35]=2[C:36]([OH:38])=[O:37])(=[O:28])=[O:29])[CH:20]=[C:21]([C:23]([F:24])([F:25])[F:26])[CH:22]=1

Participants

4

Reactant 1

HCID 131719489Benzhydrol 2-[2-[3,5-bis(trifluoromethyl)phenylsulfonamido]-4-trifluoromethylphenoxy]benzoate

Product 1

HCID 9808192SB 203347

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Benzhydrol 2-[2-[3,5-bis(trifluoromethyl)phenylsulfonamido]-4-trifluoromethylphenoxy]benzoate (3.7 g, 5 mmol) was dissolved in ethyl acetate (125 mL) and was hydrogenated for 0.75 hour at 50 psi over 10% palladium on carbon (0.5 g). The catalyst was filtered off and the solvent evaporated to give the crude product which was purified by flash chromatography (silica gel, ethyl acetate/hexane/formic acid). Recrystallization from ethyl acetate/hexane gave the title compound as a white crystalline solid; mp 133°-134° C.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent evaporated
  3. customto give the crude product which
  4. customwas purified by flash chromatography (silica gel, ethyl acetate/hexane/formic acid)
  5. customRecrystallization from ethyl acetate/hexane

Sources & evidence

ORD record
ord-8188df27541d45bdb3c9cf2331a128f2
Source dataset
uspto-grants-1996_08
Patent number
US05545669

Reaction notes

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