HuagongsheHuagongshe Chemistry Print Report · For research reference only
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
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lawesson's reagent | HCID 87949 | — |
| Reactant | N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide | HCID 9908135 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | N-[[(5S)-3-[3-fluoro-4-(tetrahydro-1,1-dioxido-2H-1,2-thiazin-4-yl)phenyl]-2-oxo-5-oxazolidinyl]methyl]ethanethioamide | HCID 9887296 | 92% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06420360B1 |
| Source dataset | uspto-grants-2002_07 |
| ORD ID | ord-5a2a35553d274f179f58a93ee9bf9fd0 |
| Source note | uspto-grants-2002_07 |