Triphenylphosphine Oxide → HCID 57476116, compound

HRID 1960307Notes

Reaction equation

HRID 1960307 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.C([S:43][C:44]([CH3:82])([CH2:59][NH:60][C:61]([C:63]1[NH:64][C:65]2[C:70]([CH:71]=1)=[CH:69][CH:68]=[CH:67][C:66]=2[N:72]([CH3:81])[S:73]([C:76]1[S:77][CH:78]=[CH:79][CH:80]=1)(=[O:75])=[O:74])=O)[CH2:45][N:46]1[CH2:51][CH2:50][N:49](C(OC(C)(C)C)=O)[CH2:48][CH2:47]1)C1C=CC=CC=1.C(=O)([O-])O.[Na+]>C(#N)C>[CH3:81][N:72]([C:66]1[CH:67]=[CH:68][CH:69]=[C:70]2[C:65]=1[NH:64][C:63]([C:61]1[S:43][C:44]([CH3:82])([CH2:45][N:46]3[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]3)[CH2:59][N:60]=1)=[CH:71]2)[S:73]([C:76]1[S:77][CH:78]=[CH:79][CH:80]=1)(=[O:75])=[O:74]

Participants

6

Reactant 4

HCID 13097Triphenylphosphine OxideHCID 67749Trifluoromethanesulfonic anhydrideHCID 516892Sodium BicarbonateHCID 59135589HCID 59135589, compound

Product 1

HCID 57476116HCID 57476116, compoundYield 45.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of triphenylphosphine oxide (3.09 g) in acetonitrile (20 ml) was slowly added trifluoromethanesulfonic anhydride (0.93 ml) at 0° C., and the mixture was stirred for 10 min. tert-Butyl 4-{2-(benzylthio)-2-methyl-3-[({7-[methyl(2-thienylsulfonyl)amino]-1H-indol-2-yl}carbonyl)amino]propyl}piperazine-1-carboxylate (1.55 g) was added, and the reaction mixture was stirred at 0° C. for 30 min. Saturated aqueous sodium hydrogencarbonate was added, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried MgSO4). 4N Hydrogen chloride-ethyl acetate solution was added to the ethyl acetate layer, and the precipitated solid was collected by filtration, and washed with ethyl acetate. The obtained solid was suspended in saturated aqueous sodium hydrogencarbonate, and the mixture was stirred for 30 min. The solid was collected by filtration, washed with water and ethyl acetate, and dried to give the title compound (0.49 g, yield 45%) as colorless crystals. melting point 178-180° C.

Workup

  1. customat 0° C.
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine, and dried MgSO4)
  5. addition4N Hydrogen chloride-ethyl acetate solution was added to the ethyl acetate layer
  6. filtrationthe precipitated solid was collected by filtration
  7. washwashed with ethyl acetate
  8. stirringthe mixture was stirred for 30 min
  9. filtrationThe solid was collected by filtration
  10. washwashed with water and ethyl acetate
  11. customdried

Sources & evidence

ORD record
ord-dc6a02d7e0ab436ca7471d5eeeeaf39a
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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