Lawesson's reagent → N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide

HRID 2229142Notes

Reaction equation

HRID 2229142 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][NH:22][C:23](=O)[CH3:24])[O:18][C:17]2=[O:26])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[NH:10][CH2:9]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][NH:22][C:23](=[S:36])[CH3:24])[O:18][C:17]2=[O:26])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[NH:10][CH2:9]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 9908135N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Product 1

HCID 9887296N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamideYield 92%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-[[(5S)-3-[3-Fluoro-4-(tetrahydro-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (180 mg, 0.47 mmol), Lawesson's Reagent (310 mg, 0.77 mmol) and dioxane (10 ml) are heated under reflux for 1 hr. After cooling, the solvent is evaporated and the residue chromatographed over silica gel (40 g) eluting with 2-4% methanol-chloroform gives the title compound as a foam (173 mg, 92%). HRMS(FAB): calcd for m+H=402.0957; Found: 402.0954.

Workup

  1. temperatureunder reflux for 1 hr
  2. temperatureAfter cooling
  3. customthe solvent is evaporated
  4. customthe residue chromatographed over silica gel (40 g)
  5. washeluting with 2-4% methanol-chloroform

Sources & evidence

ORD record
ord-5a2a35553d274f179f58a93ee9bf9fd0
Source dataset
uspto-grants-2002_07
Patent number
US06420360B1

Reaction notes

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