N-chloro-N-methyl-p-toluenesulfonamide → p-Nitrobenzyl 3-Methyl-2-(2-chlorosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate

HRID 261313

반응식

HRID 261313 반응식
[O:1]([CH2:8][C:9]([NH:11][CH:12]1[C:34](=[O:35])[N:14]2[CH:15]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=3)=[O:22])[C:16]([CH3:20])([CH3:19])[S:17](=[O:18])[C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:36]N(C)S(C1C=CC(C)=CC=1)(=O)=O>>[CH3:19][C:16](=[CH2:20])[CH:15]([N:14]1[C:34](=[O:35])[CH:12]([NH:11][C:9](=[O:10])[CH2:8][O:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:13]1[S:17]([Cl:36])=[O:18])[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][C:28]([N+:31]([O-:33])=[O:32])=[CH:27][CH:26]=1)=[O:22]

참가 물질

3

반응물 2

HCID 13017215N-chloro-N-methyl-p-toluenesulfonamideHCID 67928276p-Nitrobenzyl 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylate-1-oxide

생성물 1

HCID 9936995p-Nitrobenzyl 3-Methyl-2-(2-chlorosulfinyl-4-oxo-3-phenoxyacetamido-1-azetidinyl)-3-butenoate

실험 절차

To 150 ml. of distilled and molecular sieve-dried toluene were added 3.0 g. (6 mmol.) of p-nitrobenzyl 6-phenoxyacetamido-2,2-dimethylpenam-3-carboxylate-1-oxide and 1.3 g. (6 mmol.) of N-chloro-N-methyl-p-toluenesulfonamide. The mixture was heated at reflux for 60 minutes. The resulting reaction mixture then was cooled to room temperature. An aliquot (15 ml.) was separated, washed with water, and brine, dried over magnesium sulfate, and evaporated to dryness in vacuo. The nmr spectrum of the residue was consistent for the title compound contaminated with some N-methyl-p-toluenesulfonamide.

후처리

  1. distillationof distilled
  2. additionmolecular sieve-dried toluene were added 3.0 g
  3. temperatureThe mixture was heated
  4. temperatureat reflux for 60 minutes
  5. customThe resulting reaction mixture
  6. customAn aliquot (15 ml.) was separated
  7. washwashed with water, and brine
  8. dry with materialdried over magnesium sulfate
  9. customevaporated to dryness in vacuo

출처 및 근거

ORD 기록
ord-a641228144254f99a5c289426dabe60c
출처 데이터셋
uspto-grants-1979_08
특허 번호
US04165315

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