Triphenylphosphine Oxide → HCID 57901611, compound

HRID 1851488Notes

Reaction equation

HRID 1851488 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][C:37]1[C:45]([NH:46][S:47]([C:50]2[S:51][CH:52]=[CH:53][CH:54]=2)(=[O:49])=[O:48])=[C:44]2[C:40]([CH:41]=[C:42]([C:55]([NH:57][CH2:58][CH2:59][S:60]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)=O)[NH:43]2)=[CH:39][CH:38]=1.C(=O)([O-])O.[Na+]>ClCCl>[S:60]1[CH2:59][CH2:58][N:57]=[C:55]1[C:42]1[NH:43][C:44]2[C:40]([CH:41]=1)=[CH:39][CH:38]=[C:37]([CH3:36])[C:45]=2[NH:46][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 57901617HCID 57901617, compound

Product 1

HCID 57901611HCID 57901611, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of triphenylphosphine oxide (1.5 g), trifluoromethanesulfonic anhydride (0.46 mL) and dichloromethane (25 mL) was stirred for 15 min under ice-cooling. 6-Methyl-7-[(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (0.57 g) was added, and the mixture was stirred for 4 hr under ice-cooling. The reaction mixture 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 crystals were suspended in ethyl acetate-hexane, and the insoluble material was filtered off. The filtrate was concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography (ethyl acetate:hexane=1:9-1:3), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (251 mg, yield 74%) as colorless prism crystals. melting point 183-184° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 4 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. filtrationthe insoluble material was filtered off
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthe obtained crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-06e2fce21793422eadd486a0dfbfb784
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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