Oxalyl chloride → 2-[4-(o-Methoxybenzenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-isocrotonic acid chloride

HRID 26106Notes

Reaction equation

HRID 26106 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([S:12][CH:13]1[N:16](/[C:17](=[C:21](\[O:23][CH3:24])/[CH3:22])/[C:18](O)=[O:19])[C:15](=[O:25])[CH:14]1[NH:26][C:27](=[O:36])[CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:11])=[O:10].C(Cl)(=O)C([Cl:40])=O>CN(C)C=O.O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[S:9]([S:12][CH:13]1[N:16](/[C:17](=[C:21](\[O:23][CH3:24])/[CH3:22])/[C:18]([Cl:40])=[O:19])[C:15](=[O:25])[CH:14]1[NH:26][C:27](=[O:36])[CH2:28][O:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 705580402-[4-(o-Methoxybenzenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxyisocrotonic acid

Product 1

HCID 887582302-[4-(o-Methoxybenzenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-isocrotonic acid chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

One drop of dimethylformamide in dioxane is added to a soltuion of 54 mg (0.1 mM) of 2-[4-(o-methoxybenzensulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-isocrotonic acid in 0.5 ml of a 10% strength solution of oxalyl chloride in dioxane, whereupon an evolution of gas occurs immediately. The mixture is stirred for 2 hours at room temperature and the solvent and the excess oxalyl chloride are evaporated off in vacuo. The residue is dried in a high vacuum and gives 2-[4-(o-methoxybenzenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1yl]-3-methoxy-isocrotonic acid chloride in the form of a slightly orange-coloured foam, IR spectrum (CH2Cl2): 5.60, 5.90 and 8.70 μ.

Workup

  1. customthe solvent and the excess oxalyl chloride are evaporated off in vacuo
  2. customThe residue is dried in a high vacuum

Sources & evidence

ORD record
ord-3ad033782a3e44aabdb080e5e324165e
Source dataset
uspto-grants-1979_04
Patent number
US04147864

Reaction notes

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