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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 370503Generated: October 27, 2026

p-Toluenesulfonic acid monohydrate → Pivaloyloxymethyl 3-acetylthio-8-oxo-4,5-dithia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate

https://huagongshe.com/reaction/370503

Reaction equation

Participants

RoleNameHCIDCharge
Reactantp-Toluenesulfonic acid monohydrateHCID 521998—
ReactantPivaloyloxymethyl 3,3-di(acetylthio)-2-(4-allylsulphinylazetidin-2-on-1-yl)propenoateHCID 20275777—
Solvent1,4-DioxaneHCID 31275—
ProductPivaloyloxymethyl 3-acetylthio-8-oxo-4,5-dithia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylateHCID 2027577654%

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS04526718
Source datasetuspto-grants-1985_07
ORD IDord-99c0dfbb0c444249aa163f8b9714a71c
Source noteuspto-grants-1985_07