Lawesson's reagent → HCID 11759977, compound

HRID 1954604Notes

Reaction equation

HRID 1954604 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C@H:9]2[CH2:13][N:12]([C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[C:11](=O)[C:10]2([F:24])[F:23])[CH2:8][CH2:7]1)=[O:5])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>C1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1([C@H:9]2[CH2:13][N:12]([C@H:14]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH3:15])[C:11](=[S:34])[C:10]2([F:24])[F:23])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 10882284HCID 10882284, compound

Product 1

HCID 11759977HCID 11759977, compoundYield 150.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-(S)-(1-Ethoxycarbonylcyclopropyl)-3,3-difluoro-1-[1-(S)-phenylethyl]-2-pyrrolidone (3.621 g, 10.73 mmol) was dissolved in dry benzene (100 ml), and the solution was mixed with Lawesson's reagent (2.192 g, 5.420 mmol) and heated under reflux for 1 hour. After cooling, benzene was evaporated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography and eluted with an eluant of n-hexane:ethyl acetate=5:1, to thereby obtain 2.886 g (76.1%) of the title compound as a light yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. custombenzene was evaporated under reduced pressure
  5. washeluted with an eluant of n-hexane

Sources & evidence

ORD record
ord-65bb6631b04842e6828d35b6aab961e0
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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