Triphenylphosphine Oxide → HCID 57901818, compound

HRID 1851504Notes

Reaction equation

HRID 1851504 reaction equation
C1(P(=O)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC(F)(F)S(OS(C(F)(F)F)(=O)=O)(=O)=O.[CH3:36][S:37]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[S:46]([NH:49][C:50]1[CH:51]=[CH:52][CH:53]=[C:54]2[C:58]=1[NH:57][C:56]([C:59]([NH:61][CH2:62][CH2:63][S:64]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)=[CH:55]2)(=[O:48])=[O:47])(=[O:39])=[O:38]>ClCCl>[S:64]1[CH2:63][CH2:62][N:61]=[C:59]1[C:56]1[NH:57][C:58]2[C:54]([CH:55]=1)=[CH:53][CH:52]=[CH:51][C:50]=2[NH:49][S:46]([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=1[S:37]([CH3:36])(=[O:39])=[O:38])(=[O:48])=[O:47]

Participants

5

Reactant 3

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 57901721HCID 57901721, compound

Product 1

HCID 57901818HCID 57901818, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of triphenylphosphine oxide (4.27 g) in dichloromethane (20 mL) was slowly added trifluoromethanesulfonic anhydride (1.30 mL) at 0° C. The mixture was stirred for 10 min, and 7-{[2-(methylsulfonyl)phenylsulfonyl]amino}-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (1.78 g) was added. The reaction mixture was stirred at room temperature for 3 hr and concentrated. Saturated aqueous sodium hydrogen carbonate was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography and the title compound (0.69 g, yield 63%) was obtained as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:1, volume ratio). The crystals were recrystallized from ethyl acetate-hexane. melting point 211-212° C.

Workup

  1. customat 0° C
  2. stirringThe reaction mixture was stirred at room temperature for 3 hr
  3. concentrationconcentrated
  4. additionSaturated aqueous sodium hydrogen carbonate was added
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e9171868481e48ec900e6ef7f10132df
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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