Lawesson's reagent → HCID 57650584, compound

HRID 2063475Notes

Reaction equation

HRID 2063475 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([C@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=O)[CH3:9])=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([NH:10][C:11]([C@H:13]2[CH2:17][CH2:16][CH2:15][N:14]2[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[S:34])[CH3:9])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 87949Lawesson's reagentHCID 51968676HCID 51968676, compound

Product 1

HCID 57650584HCID 57650584, compoundYield 140.3%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture the product of Step A (3 g, 8.5 mmol) and Lawesson's reagent (1.7 g, 4.25 mmol) in toluene (100 ml) was refluxed for 2 h. The mixture was cooled to room temperature and then was diluted with EtOAc (100 ml), washed with 1N NaOH (2×50 ml), dried over Na2SO4, and concentrated in vacuo. Flash chromatography purification (DCM/MeOH gradient, 0-15% MeOH) provided the desired product as a white solid (2.2 g, 71%)

Workup

  1. washwashed with 1N NaOH (2×50 ml)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customFlash chromatography purification (DCM/MeOH gradient, 0-15% MeOH)

Sources & evidence

ORD record
ord-ca4068071ae64372bd408429d756ddfd
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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