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

HRID 370503Notes

Reaction equation

HRID 370503 reaction equation
[C:1]([S:4][C:5]([S:28]C(=O)C)=[C:6]([N:18]1[CH:21]([S:22](CC=C)=O)[CH2:20][C:19]1=[O:27])[C:7]([O:9][CH2:10][O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:8])(=[O:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>O1CCOCC1>[C:1]([S:4][C:5]1[S:28][S:22][CH:21]2[N:18]([C:19](=[O:27])[CH2:20]2)[C:6]=1[C:7]([O:9][CH2:10][O:11][C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 20275777Pivaloyloxymethyl 3,3-di(acetylthio)-2-(4-allylsulphinylazetidin-2-on-1-yl)propenoate

Product 1

HCID 20275776Pivaloyloxymethyl 3-acetylthio-8-oxo-4,5-dithia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

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.

Workup

  1. temperatureto reflux
  2. temperaturemaintained
  3. temperatureunder reflux for 1 hour
  4. customThe solvent was removed by evaporation
  5. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-99c0dfbb0c444249aa163f8b9714a71c
Source dataset
uspto-grants-1985_07
Patent number
US04526718

Reaction notes

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