Triphenylphosphine Oxide → HCID 57901703, compound

HRID 1851560Notes

Reaction equation

HRID 1851560 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.[F:36][C:37]1[CH:38]=[C:39]2[C:43](=[C:44]([N:46]([CH3:55])[S:47]([C:50]3[S:51][CH:52]=[CH:53][CH:54]=3)(=[O:49])=[O:48])[CH:45]=1)[NH:42][C:41]([C:56]([NH:58][CH2:59][CH2:60][S:61]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)=[CH:40]2.C(=O)([O-])O.[Na+]>ClCCl>[S:61]1[CH2:60][CH2:59][N:58]=[C:56]1[C:41]1[NH:42][C:43]2[C:39]([CH:40]=1)=[CH:38][C:37]([F:36])=[CH:45][C:44]=2[N:46]([CH3:55])[S:47]([C:50]1[S:51][CH:52]=[CH:53][CH:54]=1)(=[O:49])=[O:48]

Participants

6

Reactant 4

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 57901825HCID 57901825, compound

Product 1

HCID 57901703HCID 57901703, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of triphenylphosphine oxide (522 mg), trifluoromethanesulfonic anhydride (0.158 mL), and dichloromethane (10 mL) was stirred for 15 min under ice-cooling. Then, 5-fluoro-7-[methyl(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (205 mg) was added, and the mixture was stirred for 3 hr under ice-cooling. The reaction solution was poured into aqueous sodium hydrogencarbonate solution and extracted with dichloromethane. The aqueous layer was extracted with dichloromethane, and the combined dichloromethane layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=2:8-5:5), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (92 mg, yield 75%) as colorless prism crystals. melting point 188-189° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 3 hr under ice-
  3. temperaturecooling
  4. extractionextracted with dichloromethane
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. dry with materialthe combined dichloromethane layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customthe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-c621df22cf1e4d57aadf8c0c214e41be
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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