Triphenylphosphine Oxide → HCID 57901733, compound

HRID 1851473Notes

Reaction equation

HRID 1851473 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]([CH3:46])=[CH:44][C:43]([NH:47][S:48]([C:51]2[S:52][CH:53]=[CH:54][CH:55]=2)(=[O:50])=[O:49])=[C:42]2[C:38]=1[CH:39]=[C:40]([C:56]([NH:58][CH2:59][CH2:60][S:61]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=O)[NH:41]2.C(=O)([O-])O.[Na+]>ClCCl>[S:61]1[CH2:60][CH2:59][N:58]=[C:56]1[C:40]1[NH:41][C:42]2[C:38]([CH:39]=1)=[C:37]([CH3:36])[C:45]([CH3:46])=[CH:44][C:43]=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 57901585HCID 57901585, compound

Product 1

HCID 57901733HCID 57901733, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of triphenylphosphine oxide (1.1 g), trifluoromethanesulfonic anhydride (0.31 mL) and dichloromethane (20 mL) was stirred for 10 min under ice-cooling. 4,5-Dimethyl-7-[(2-thienylsulfonyl)amino]-N-[2-(tritylthio)ethyl]-1H-indole-2-carboxamide (0.40 g) was added, and the mixture was stirred for 3 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 residue was subjected to silica gel column chromatography (ethyl acetate:hexane=3:7-5:5), and the obtained crystals were recrystallized from ethyl acetate-hexane to give the title compound (201 mg, yield 84%) as colorless prism crystals. melting point 201-202° 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-a9c1c18aef754716a4026986875f01a1
Source dataset
uspto-grants-2015_02
Patent number
US08957070B2

Reaction notes

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