Water → p-Nitrobenzyl 2-(3-phenylacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-chloromethyl-3-butenate

HRID 414126Notes

Reaction equation

HRID 414126 reaction equation
[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[CH:14]([S:15][S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:18])=[O:17])[N:13]([CH:25]([C:39]([CH3:41])=[CH2:40])[C:26]([O:28][CH2:29][C:30]3[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=3)=[O:27])[C:12]2=[O:42])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O(Cl)[Cl:44].O>C(OCCOCC)(=O)C.C(Cl)(Cl)(Cl)Cl>[C:1]1([CH2:7][C:8]([NH:10][CH:11]2[CH:14]([S:15][S:16]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)(=[O:18])=[O:17])[N:13]([CH:25]([C:39]([CH2:41][Cl:44])=[CH2:40])[C:26]([O:28][CH2:29][C:30]3[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=3)=[O:27])[C:12]2=[O:42])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24646Chlorine monoxideHCID 13530981p-Nitrobenzyl 2-(3-phenylacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-methyl-3-butenate

Product 1

HCID 15702741p-Nitrobenzyl 2-(3-phenylacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-chloromethyl-3-butenateYield 90%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8095Glycol monoethyl ether acetateSolvent

Procedure

A 1.0 g quantity of p-nitrobenzyl 2-(3-phenylacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-methyl-3-butenate was dissolved in 25 ml of ethoxyethyl acetate. The solution was cooled in an ice bath with stirring. To the mixture was added dropwise over 20 minutes 6.l ml of a 0.285M solution of Cl2O in carbon tetrachloride. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. The solvent was distilled off at reduced pressure. The resulting residue was separated and purified by silica gel column chromatography, giving 955 mg of p-nitrobenzyl 2-(3-phenylacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-chloromethyl-3-butenate in 90% yield.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off at reduced pressure
  5. customThe resulting residue was separated
  6. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-b93d40e73120489faf282b43523baee1
Source dataset
uspto-grants-1988_12
Patent number
US04789740

Reaction notes

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