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

HRID 1699662Notes

Reaction equation

HRID 1699662 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22][NH:23][C:24](=O)[CH3:25])[O:19][C:18]2=[O:27])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[N:10]([CH3:16])[CH2:9]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>O1CCOCC1>[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22][NH:23][C:24](=[S:37])[CH3:25])[O:19][C:18]2=[O:27])[CH:5]=[CH:6][C:7]=1[CH:8]1[CH2:13][CH2:12][S:11](=[O:15])(=[O:14])[N:10]([CH3:16])[CH2:9]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 9865662N-[[(5S)-3-[3-fluoro-4-(tetrahydro-2-methyl-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Product 1

HCID 9801952N-[[(5S)-3-[3-fluoro-4-(tetrahydro-2-methyl-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamideYield 85.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

N-[[(5S)-3-[3-fluoro-4-(tetrahydro-2-methyl-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide (100 mg, 0.25 mmol) and Lawesson's Reagent (122 mg, 0.30 mmol) were dissolved in dioxane (10 mL) under nitrogen. The reaction is heated to 100° C. for 20 minutes then cooled to ambient and evaporated. The residue is partitioned between ethyl acetate (150 mL) and water (50 mL). The organic phase is washed 3 times with water (50 mL) and brine (50 mL), then dried over MgSO4, filtered and evaporated to a nearly colorless glass. The product is purified by radial chromatography over silica gel, eluting with 0-10% methanol-methylene chloride to give a white solid foam (89 mg, 85%). MP=95-98° C., decomposes.

Workup

  1. temperaturethen cooled
  2. customevaporated
  3. customThe residue is partitioned between ethyl acetate (150 mL) and water (50 mL)
  4. washThe organic phase is washed 3 times with water (50 mL) and brine (50 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated to a nearly colorless glass
  8. customThe product is purified by radial chromatography over silica gel
  9. washeluting with 0-10% methanol-methylene chloride

Sources & evidence

ORD record
ord-8fef08a810244b51ba87e3e4e2b97e1e
Source dataset
uspto-grants-2002_02
Patent number
US06348459B1

Reaction notes

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