Triphenylphosphine → 1,1,1-trifluoro-N-(4-[5-fluoro-2-(trifluoromethyl)phenyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}cyclohexyl)methanesulfonamide

HRID 1914256Notes

Reaction equation

HRID 1914256 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:28]([F:31])([F:30])[F:29])=[C:6]([C:8]2([S:15]([C:18]3[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=3)(=[O:17])=[O:16])[CH2:13][CH2:12][CH:11](O)[CH2:10][CH2:9]2)[CH:7]=1.[F:32][C:33]([F:39])([F:38])[S:34]([NH2:37])(=[O:36])=[O:35].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:32][C:33]([F:39])([F:38])[S:34]([NH:37][CH:11]1[CH2:12][CH2:13][C:8]([C:6]2[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=2[C:28]([F:31])([F:30])[F:29])([S:15]([C:18]2[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][CH:19]=2)(=[O:17])=[O:16])[CH2:9][CH2:10]1)(=[O:36])=[O:35]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 79001TrifluoromethylsulfonamideHCID 5363146Diisopropyl azodicarboxylateHCID 584850604-[5-Fluoro-2-(trifluoromethyl)phenyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}cyclohexanol

Product 1

HCID 462442751,1,1-trifluoro-N-(4-[5-fluoro-2-(trifluoromethyl)phenyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}cyclohexyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A 2 L 3-neck round bottom flask equipped with a nitrogen bubbler, thermocouple, stir bar, heating mantle and condenser was charged with 4-[5-fluoro-2-(trifluoromethyl)phenyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}cyclohexanol (94.7 g, 201 mmol) in THF (1 L). Trifluoromethanesulfonamide (45.0 g, 302 mmol) and triphenylphosphine (79 g, 302 mmol) were added, followed by DIAD (0.059 L, 302 mmol,) which was added dropwise over 20 min. The reaction was heated to 60° C. and stirred for 18 hrs at 60° C. The reaction was concentrated and dissolved in CH2Cl2 and purified by column chromatography on silica gel, eluting with ethyl acetate/heptanes to provide 1,1,1-trifluoro-N-(4-[5-fluoro-2-(trifluoromethyl)phenyl]-4-{[4-(trifluoromethyl)phenyl]sulfonyl}cyclohexyl)methanesulfonamide.

Workup

  1. customA 2 L 3-neck round bottom flask equipped with a nitrogen bubbler
  2. temperatureheating mantle
  3. additionwas added dropwise over 20 min
  4. stirringstirred for 18 hrs at 60° C
  5. concentrationThe reaction was concentrated
  6. dissolutiondissolved in CH2Cl2
  7. custompurified by column chromatography on silica gel
  8. washeluting with ethyl acetate/heptanes

Sources & evidence

ORD record
ord-441a710d59ce4f2686f4c32a09a733e9
Source dataset
uspto-grants-2013_12
Patent number
US08609897B2

Reaction notes

Loading…