Sodium Chloride → 2-[4-(p-Toluenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-isocrotonic acid diphenylmethyl ester

HRID 26097Notes

Reaction equation

HRID 26097 reaction equation
[CH3:1]OS(OC)(=O)=O.[C:8]1([CH:14]([O:21][C:22](=[O:54])/[C:23](/[N:27]2[CH:30]([S:31][S:32]([C:35]3[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=3)(=[O:34])=[O:33])[CH:29]([NH:42][C:43](=[O:52])[CH2:44][O:45][C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)[C:28]2=[O:53])=[C:24](\[OH:26])/[CH3:25])[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH-].[Na+].[Cl-].[Na+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.C(Cl)(Cl)(Cl)Cl.O.C(OCC)(=O)C>[C:8]1([CH:14]([O:21][C:22](=[O:54])/[C:23](/[N:27]2[CH:30]([S:31][S:32]([C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=3)(=[O:33])=[O:34])[CH:29]([NH:42][C:43](=[O:52])[CH2:44][O:45][C:46]3[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=3)[C:28]2=[O:53])=[C:24](/[O:26][CH3:1])\[CH3:25])[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

9

Reactant 4

HCID 5234Sodium ChlorideHCID 6497Dimethyl SulfateHCID 14798Sodium Hydroxide2×HCID 70454173HCID 70454173, compound

Product 1

HCID 128054242-[4-(p-Toluenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-isocrotonic acid diphenylmethyl ester

Reagents, catalysts & solvents 4

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent2×HCID 5943Carbon TetrachlorideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(avii) 1.08 g (3 mmols) of tetrabutylammonium iodide and 1.9 ml (2.52 g, 20 mmols) of dimethylsulphate are added to a suspension of 3.36 g (5 mmols) of 2-[4-(p-toluenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-hydroxy-crotonic acid diphenylmethyl ester (crystalline) in 15 ml of carbon tetrachloride and 10 ml of water. The mixture is vigorously stirred at room temperature and 1 N sodium hydroxide solution is added to it by means of an automatic titrator in sufficient amount to keep the pH constant at 7.0. In the course of 4-5 hours, 1.5-2 equivalents of sodium hydroxide solution are consumed. The mixture is diluted with ethyl acetate and water and a little sodium chloride is added. The organic phase is dried over sodium sulphate and concentrated by evaporation. The residue is crystallised from a little ethyl acetate/hexane, 1:1, and gives 2-[4-(p-toluenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methoxy-iso-crotonic acid diphenylmethyl ester.

Workup

  1. dry with materialThe organic phase is dried over sodium sulphate
  2. concentrationconcentrated by evaporation
  3. customThe residue is crystallised from a little ethyl acetate/hexane, 1:1

Sources & evidence

ORD record
ord-614d5a01bd7f4c77bb8b2d5bce37ad99
Source dataset
uspto-grants-1979_04
Patent number
US04147864

Reaction notes

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