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

HRID 543600Notes

Reaction equation

HRID 543600 reaction equation
S(Cl)([Cl:3])=O.[N+:5]([C:8]1[CH:28]=[CH:27][C:11]([CH2:12][O:13][C:14](=[O:26])[CH:15]([N:17]2[C@H:20]([S:21][C:22](=[O:24])[CH3:23])[CH2:19][C:18]2=[O:25])O)=[CH:10][CH:9]=1)([O-:7])=[O:6]>O1CCOCC1>[N+:5]([C:8]1[CH:28]=[CH:27][C:11]([CH2:12][O:13][C:14](=[O:26])[CH:15]([N:17]2[C@H:20]([S:21][C:22](=[O:24])[CH3:23])[CH2:19][C:18]2=[O:25])[Cl:3])=[CH:10][CH:9]=1)([O-:7])=[O:6]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 538127912-[(4R)-4-Acetylthio-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl ester

Product 1

HCID 539515252-[(4R)-4-acetylthio-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 2.86 g (~24 mmol) of thionyl chloride in 20 ml of dioxan is added dropwise to a suspension, stirred at room temperature, of 12 g of poly-Hunig base in a solution of 2.83 g (7.59 mmol) of 2-[(4R)-4-acetylthio-2-oxoazetidin-1-yl]-2-hydroxyacetic acid p-nitrobenzyl ester in 100 ml of dioxan. The mixture is stirred for 1.5 hours at room temperature and filtered off from the poly-Hunig base, which is subsequently washed with dioxan. The filtrate is concentrated in vacuo. The 2-[(4R)-4-acetylthio-2-oxoazetidin-1-yl]-2-chloroacetic acid p-nitrobenzyl ester obtained is used in the next stage in crude form.

Workup

  1. filtrationfiltered off from the poly-Hunig base, which
  2. washis subsequently washed with dioxan
  3. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-5d41747b9fab48fbb226e278534a48ff
Source dataset
uspto-grants-1984_05
Patent number
US04447360

Reaction notes

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