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Ethyl Acetate → Racemic 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(3-nitrophenylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate

HRID 1376835
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HRID 1376835 반응식
P(I)(I)P(I)I.[C:7]([NH:26][C:27]1[S:28][CH:29]=[C:30]([C:32](=[N:63][O:64][CH3:65])[C:33]([NH:35][CH:36]2[C:43](=[O:44])[N:42]3[CH:37]2[CH2:38][S:39][CH:40]([S:53][C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([N+:60]([O-:62])=[O:61])[CH:55]=2)[C:41]3(O)[C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[O:34])[N:31]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.C(OCC)(=O)C>N1C=CC=CC=1>[C:7]([NH:26][C:27]1[S:28][CH:29]=[C:30]([C:32](=[N:63][O:64][CH3:65])[C:33]([NH:35][CH:36]2[C:43](=[O:44])[N:42]3[CH:37]2[CH2:38][S:39][C:40]([S:53][C:54]2[CH:59]=[CH:58][CH:57]=[C:56]([N+:60]([O-:62])=[O:61])[CH:55]=2)=[C:41]3[C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])=[O:34])[N:31]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 83484Hypodiphosphorous tetraiodide2회HCID 537770691,1-Dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-2-hydroxy-3-(3-nitrophenylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]octane-2-carboxylate

생성물 1

HCID 53941303Racemic 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(3-nitrophenylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate
수율 45.6%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

A suspension of 677 mg of diphosphorus tetraiodide in 7 ml of pyridine was stirred under an inert atmosphere for 5 minutes and then 780 mg of the product of Step A were added. The mixture was stirred for 2 hours and then a further 363 mg of diphosphorus tetraiodide were added. The stirring was maintained for 1 hour and the reaction mixture was poured into 50 ml of ethyl acetate and filtered. The filtrate was evaporated to dryness under reduced pressure and the residue was dissolved in methylene chloride. The organic phase was washed with 0.1N hydrochloric acid, then with water, dried and concentrated to dryness. The residue was chromatographed on silica and eluted with a mixture of chloroform and acetone (10-0.5) to obtain 348 mg of racemic 1,1-dimethylethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-(3-nitrophenylthio)-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylate which crystallized from ether.

후처리

  1. stirringThe mixture was stirred for 2 hours
  2. temperatureThe stirring was maintained for 1 hour
  3. filtrationfiltered
  4. customThe filtrate was evaporated to dryness under reduced pressure
  5. dissolutionthe residue was dissolved in methylene chloride
  6. washThe organic phase was washed with 0.1N hydrochloric acid
  7. dry with materialwith water, dried
  8. concentrationconcentrated to dryness
  9. customThe residue was chromatographed on silica
  10. washeluted with a mixture of chloroform and acetone (10-0.5)

출처 및 근거

ORD 기록
ord-1fd019655fe64d5780bc8451a36df9b7
출처 데이터셋
uspto-grants-1997_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05663164

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