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

HRID 414124

反応式

HRID 414124 の反応式
[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:42].O>C(OC(OCC)C)C.C(OCC)C>[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

参加物

6

反応物 3

HCID 962WaterHCID 24341Hypochlorous AcidHCID 13170072Benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinon-1-yl)-3-methyl-3butenoate

生成物 1

HCID 13170074Benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-chloromethyl-3-butenate収率 90%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 7765Acetal溶媒

実験手順

A 200 mg quantity of benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-methyl-3-butenate was dissolved in 4.3 ml of diethoxyethane. The solution was cooled in an ice bath with stirring. Thereto was added dropwise over 3 minutes 1.73 ml of a 0.3M solution of HOCl in diethyl ether. 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 191 mg of benzyl 2-(3-phenoxyacetamido-4-benzenesulfonylthio-2-azetidinone-1-yl)-3-chloromethyl-3-butenate in 90% yield.

後処理

  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

出典と根拠

ORDレコード
ord-9ddbed2d352646b08249bd48e3f30623
出典データセット
uspto-grants-1988_12
特許番号
US04789740

関連ノート

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