Thionyl Chloride → 2-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester

HRID 1710238Notes

Reaction equation

HRID 1710238 reaction equation
[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([CH2:8][O:9][C:10](=[O:24])[CH:11]([N:13]2[C@H:16]([S:17][C:18](=[O:20])[CH3:19])[C@@H:15]([O:21][CH3:22])[C:14]2=[O:23])O)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)([Cl:29])=O>O1CCOCC1>[N+:1]([C:4]1[CH:26]=[CH:25][C:7]([CH2:8][O:9][C:10](=[O:24])[CH:11]([N:13]2[C@H:16]([S:17][C:18](=[O:20])[CH3:19])[C@@H:15]([O:21][CH3:22])[C:14]2=[O:23])[Cl:29])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 566076512-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl ester

Product 1

HCID 566132492-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent3×

Procedure

A suspension of 2 g of poly-Hunig base in 8 ml of dioxan is stirred for 30 minutes at room temperature, 832 mg of 2-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl ester dissolved in 12 ml of dioxan are added and then slowly a solution of 0.54 ml of thionyl chloride in 10 ml of dioxan is added. The mixture is stirred for 2 hours at room temperature, the poly-Hunig base is filtered off and the filtrate is concentrated by evaporation in vacuo. The residue is purified by chromatography over silica gel with toluene/ethyl acetate (1:1) and yields the 2-[(3S,4R)-4-acetylthio-3-methoxy-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester in crude form.

Workup

  1. additionare added
  2. stirringThe mixture is stirred for 2 hours at room temperature
  3. filtrationthe poly-Hunig base is filtered off
  4. concentrationthe filtrate is concentrated by evaporation in vacuo
  5. customThe residue is purified by chromatography over silica gel with toluene/ethyl acetate (1:1)

Sources & evidence

ORD record
ord-94dfcc42a2314117998ba5b0af10b330
Source dataset
uspto-grants-1990_08
Patent number
US04952690

Reaction notes

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