HuagongsheHuagongshe Chemistry Print Report · For research reference only
p-Toluenesulfonic acid monohydrate → Pivaloyloxymethyl 3-acetylthio-8-oxo-4,5-dithia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | p-Toluenesulfonic acid monohydrate | HCID 521998 | — |
| Reactant | Pivaloyloxymethyl 3,3-di(acetylthio)-2-(4-allylsulphinylazetidin-2-on-1-yl)propenoate | HCID 20275777 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | Pivaloyloxymethyl 3-acetylthio-8-oxo-4,5-dithia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate | HCID 20275776 | 54% |
Reaction Steps
A solution of 82 mg of pivaloyloxymethyl 3,3-di(acetylthio)-2-(4-allylsulphinylazetidin-2-on-1-yl)propenoate and 32 mg of 4-toluenesulphonic acid hydrate in 10 ml of dioxan was heated rapidly to reflux and maintained under reflux for 1 hour. The solvent was removed by evaporation and the residue chromatographed on silica gel using ethyl acetate/hexane mixtures as eluant. The product (35 mg, 54%) was obtained as a yellow oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04526718 |
| Source dataset | uspto-grants-1985_07 |
| ORD ID | ord-99c0dfbb0c444249aa163f8b9714a71c |
| Source note | uspto-grants-1985_07 |