Triphenylphosphine Oxide → HCID 57901727, compound

HRID 1851492Notes

Reaction equation

HRID 1851492 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][O:37][C:38]1[CH:39]=[C:40]2[C:44](=[C:45]([NH:47][S:48]([C:51]3[S:52][CH:53]=[CH:54][CH:55]=3)(=[O:50])=[O:49])[CH:46]=1)[NH:43][C:42]([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:41]2.C(=O)([O-])O.[Na+]>ClCCl>[S:61]1[CH2:60][CH2:59][N:58]=[C:56]1[C:42]1[NH:43][C:44]2[C:40]([CH:41]=1)=[CH:39][C:38]([O:37][CH3:36])=[CH:46][C:45]=2[NH:47][S:48]([C:51]1[S:52][CH:53]=[CH:54][CH:55]=1)(=[O:49])=[O:50]

Participants

6

Reactant 4

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 57901820HCID 57901820, compound

Product 1

HCID 57901727HCID 57901727, compoundYield 42.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of triphenylphosphine oxide (1.15 g), trifluoromethanesulfonic anhydride (0.35 mL) and dichloromethane (12 mL) was stirred for 15 min under ice-cooling. 5-Methoxy-7-[(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (0.45 g) was added, and the mixture was stirred for 2 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=25:75-40:60), and the obtained oil was crystallized from ethyl acetate-hexane to give the title compound (114 mg, yield 42%) as pale-yellow prism crystals. melting point 188-189° C.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 2 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 oil was crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-d431ec92baff4cb6a9df7af362e63938
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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