Potassium Iodide → (4-Nitrophenyl)methyl (2R-(1(E),2alpha,3alpha))-alpha-(1-hydroxyethylidene)-4-oxo-3-((phenoxyacetyl)amino)-2-(((p-tolyl)sulphonyl)thio)azetidine-1-acetate

HRID 26095

반응식

HRID 26095 반응식
[N+:1]([C:4]1[CH:44]=[CH:43][C:7]([CH2:8][O:9][C:10](=[O:42])[CH:11]([N:15]2[CH:18]([S:19][S:20]([C:23]3[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=3)(=[O:22])=[O:21])[CH:17]([NH:30][C:31](=[O:40])[CH2:32][O:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:16]2=[O:41])[C:12](=[CH2:14])C)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(=O)(O)[O-:46].[Na+].[I-].[K+]>C(OC)(=O)C.O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:44]=[CH:43][C:7]([CH2:8][O:9][C:10](=[O:42])/[C:11](/[N:15]2[CH:18]([S:19][S:20]([C:23]3[CH:24]=[CH:25][C:26]([CH3:29])=[CH:27][CH:28]=3)(=[O:21])=[O:22])[CH:17]([NH:30][C:31](=[O:40])[CH2:32][O:33][C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:16]2=[O:41])=[C:12](\[OH:46])/[CH3:14])=[CH:6][CH:5]=1)([O-:3])=[O:2]

참가 물질

7

반응물 3

HCID 4875Potassium IodideHCID 128048172-[4-(p-Toluenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylenebutyric acid p-nitrobenzyl esterHCID 23665763Sodium Bisulfite

생성물 1

HCID 54709824(4-Nitrophenyl)methyl (2R-(1(E),2alpha,3alpha))-alpha-(1-hydroxyethylidene)-4-oxo-3-((phenoxyacetyl)amino)-2-(((p-tolyl)sulphonyl)thio)azetidine-1-acetate

시약·촉매·용매 3

HCID 962Water용매HCID 6584Methyl Acetate용매HCID 8857Ethyl Acetate용매

실험 절차

(di) The crude 2-[4-(p-toluenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-methylene-butyric acid p-nitrobenzyl ester obtained according to Example 1.cvii) is dissolved in 20 ml of methyl acetate and ozonised at -70° C. until starting material is no longer present, according to a thin layer chromatogram. A stream of nitrogen is then passed through the solution and the latter is warmed to 0°-5° C. A solution of 300 mg of sodium bisulphite in 5 ml of water is added and the mixture is stirred for about 5 minutes until no further ozonide is detectable by means of potassium iodide/-starch paper. The mixture is diluted with ethyl acetate, the aqueous phase is separated off and the organic phase is washed with water, dried over magnesium sulphate and freed from the solvent in vacuo. The crude product is dissolved in 3 ml of methylene chloride and 15 ml of toluene are added. The precipitate is filtered off and the filtrate is concentrated by evaporation in vacuo. The residue is recrystallised from methanol and gives 2-[4-(p-toluenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-hydroxy-crotonic acid p-nitrobenzyl ester of melting point 159°-160° C. 155°-

후처리

  1. customozonised at -70° C.
  2. temperaturethe latter is warmed to 0°-5° C
  3. customthe aqueous phase is separated off
  4. washthe organic phase is washed with water
  5. dry with materialdried over magnesium sulphate
  6. dissolutionThe crude product is dissolved in 3 ml of methylene chloride
  7. addition15 ml of toluene are added
  8. filtrationThe precipitate is filtered off
  9. concentrationthe filtrate is concentrated by evaporation in vacuo
  10. customThe residue is recrystallised from methanol

출처 및 근거

ORD 기록
ord-099d1d96a1934f8ea4805675e0fdab5f
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04147864

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