Lawesson's reagent → HCID 15524177, compound

HRID 1954586Notes

Reaction equation

HRID 1954586 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@@H:10]2[CH3:23])[CH2:8][CH2:7]1)=[O:5])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:33])=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:33])[C@@H:10]2[CH3:23])[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 15524176HCID 15524176, compound

Product 1

HCID 15524177HCID 15524177, compoundYield 167.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(3R,4S)-4-(1-Ethoxycarbonylcyclopropyl)-3-methyl-1-[(S)-1-phenylethyl]-2-pyrrolidone (1.85 g, 5.87 mmol) was dissolved in benzene (100 ml), and the solution was mixed with Lawesson's reagent (1.31 g, 3.24 mmol) and heated under reflux for 20 minutes. After completing the reaction, the solvent was evaporated and the resulting residue was purified by silica gel column chromatography (silica gel, 160 ml; ethyl acetate:hexane=1:4), to thereby obtain 1.80 g (92%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 20 minutes
  3. customthe reaction
  4. customthe solvent was evaporated
  5. customthe resulting residue was purified by silica gel column chromatography (silica gel, 160 ml; ethyl acetate:hexane=1:4)

Sources & evidence

ORD record
ord-58d81a95b99e45e0a2c22d0b1f468f57
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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