Lawesson's reagent → HCID 10309055, compound

HRID 431586Notes

Reaction equation

HRID 431586 reaction equation
[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[N:12]([C@@H:18]([CH3:22])[C:19]([NH2:21])=O)[C:11]3=[O:23])=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1>O1CCCC1>[F:1][C:2]1[CH:25]=[CH:24][C:5]([CH2:6][O:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[N:12]([C@@H:18]([CH3:22])[C:19]([NH2:21])=[S:35])[C:11]3=[O:23])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 10193511HCID 10193511, compound

Product 1

HCID 10309055HCID 10309055, compoundYield 36.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (S)-2-[5-(4-fluoro-benzyloxy)-1,3-dioxo-1,3-dihydro-isoindol-2-yl]-propionamide (171 mg, 0.5 mmol) and Lawesson's reagent (243 mg, 0.6 mmol) in tetrahydrofuran (20 mL) was stirrred at room temperature for 72 h. Then the mixture was evaporated and the residue was purified by chromatography (SiO2, CH2Cl2:2N NH3/MeOH 99:1 to 19:1) to afford the title compound (65 mg, 36%) as an off-white solid after recrystallisation from MeOH. MS: m/e=359.2 (M+H+).

Workup

  1. customThen the mixture was evaporated
  2. customthe residue was purified by chromatography (SiO2, CH2Cl2:2N NH3/MeOH 99:1 to 19:1)

Sources & evidence

ORD record
ord-ef2146d6b66e40d2ad1097bd5832ab7e
Source dataset
uspto-grants-2003_12
Patent number
US06660736B2

Reaction notes

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