HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lawesson's reagent → tert-butyl (2S,4RS)-4-(3-phenylpropyl)-5-thioxo-2-pyrrolidinecarboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lawesson's reagent | HCID 87949 | — |
| Reactant | tert-butyl (2S,4R)-5-oxo-4-(3-phenylpropyl)-2-pyrrolidinecarboxylate | HCID 86587563 | — |
| Solvent | Benzene | HCID 241 | — |
| Product | tert-butyl (2S,4RS)-4-(3-phenylpropyl)-5-thioxo-2-pyrrolidinecarboxylate | HCID 86587564 | 179.8% |
Reaction Steps
A mixture of pyroglutamate 8c (245.4 mg, 0.809 mmol) and Lawesson's reagent (164 mg, 0.404 mmol) in 6 mL benzene was stirred at reflux for 17 h, then concentrated. The crude product was purified by flash chromatography (0.5 to 1 to 1.5 to 2% MeOH/CHCl3) to afford 232 mg (90%) of the thiolactam 8d as a 2:1 mixture of diastereomers.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US06653295B2 |
| Source dataset | uspto-grants-2003_11 |
| ORD ID | ord-f0757e6051c04cb4b4ab1d61176dad8b |
| Source note | uspto-grants-2003_11 |