Lawesson's reagent → HCID 54568959, compound

HRID 1003209Notes

Reaction equation

HRID 1003209 reaction equation
[NH:1]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:2][C:3]([N:5]1[CH2:13][CH2:12][CH2:11][C@H:6]1[C:7]([O:9][CH3:10])=[O:8])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>C1(C)C=CC=CC=1>[CH3:10][O:9][C:7](=[O:8])[C@@H:6]1[CH2:11][CH2:12][CH2:13][N:5]1[C:3](=[S:30])[CH2:2][NH:1][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 53986628HCID 53986628, compound

Product 1

HCID 54568959HCID 54568959, compoundYield 132.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To Boc-Gly-Pro-OMe (2.78 g, 9.72 mmol) in toluene (200 mL) was added Lawesson's reagent (2.36 g, 5.83 mmol). The mixture was heated to reflux for 2 h, then allowed to cool to RT and concentrated under vacuum to give a yellow residue. Flash chromatography (30% EtOAc/hexanes, silica gel) gave 2.33 g (76%) of the desired compound as a yellow oil. This was homogeneous by TLC and 1H NMR analysis and was used without further purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 2 h
  3. concentrationconcentrated under vacuum
  4. customto give a yellow residue

Sources & evidence

ORD record
ord-cb0b7abbd7ce4e2e91e26070b712e8e4
Source dataset
uspto-grants-2000_04
Patent number
US06046197

Reaction notes

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