Water → Benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-chloromethyl-3-butenate

HRID 414122Notes

Reaction equation

HRID 414122 reaction equation
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15]([S:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[N:14]([CH:26]([C:37]([CH3:39])=[CH2:38])[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:28])[C:13]1=[O:40])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O(Cl)[Cl:42].O>C(OCCOCC)(=O)C.C(Cl)(Cl)(Cl)Cl>[O:1]([CH2:8][C:9]([NH:11][CH:12]1[CH:15]([S:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[N:14]([CH:26]([C:37]([CH2:39][Cl:42])=[CH2:38])[C:27]([O:29][CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)=[O:28])[C:13]1=[O:40])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 962WaterHCID 24646Chlorine monoxideHCID 13170072Benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3butenoate

Product 1

HCID 13170074Benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-chloromethyl-3-butenateYield 95%

Reagents, catalysts & solvents 2

HCID 5943Carbon TetrachlorideSolventHCID 8095Glycol monoethyl ether acetateSolvent

Procedure

A 200 mg quantity of benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-methyl-3-butenate was dissolved in 5 ml of ethoxyethyl acetate. The solution was cooled in an ice bath with stirring. Thereto was added dropwise over 10 minutes 1.21 ml of a 0.285M solution of Cl2O in carbon tetrachloride. Water was added to the reaction mixture and the resulting 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 202 mg of benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-chloromethyl-3-butenate in 95% yield.

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. extractionthe resulting 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-0fcebac8a6174d4a9b02f6bd61b11380
Source dataset
uspto-grants-1988_12
Patent number
US04789740

Reaction notes

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