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Dimethylformamide → 4-Nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate

HRID 364590
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HRID 364590 반응식
S(Cl)(C)(=O)=O.[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:41][O:42][CH3:43])[C:15]([NH:17][CH:18]2[C:39](=[O:40])[N:20]3[CH:21]([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][C:33]([N+:36]([O-:38])=[O:37])=[CH:32][CH:31]=4)=[O:27])[CH:22](O)[CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1)=[O:7].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O.C(OCC)(=O)C>[CH:6]([NH:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:41][O:42][CH3:43])[C:15]([NH:17][CH:18]2[C:39](=[O:40])[N:20]3[C:21]([C:26]([O:28][CH2:29][C:30]4[CH:31]=[CH:32][C:33]([N+:36]([O-:38])=[O:37])=[CH:34][CH:35]=4)=[O:27])=[CH:22][CH2:23][S:24][C@H:19]23)=[O:16])[N:13]=1)=[O:7]
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참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 1317124974-Nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-hydroxycepham-4-carboxylate

생성물 1

HCID 1317124414-Nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate수율 12.4%

시약·촉매·용매 2

HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

Mesyl chloride (0.406 g.) was dropwise added to a stirred mixture of 4-nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-hydroxycepham-4-carboxylate (syn isomer, 1 g.), N,N-dimethylformamide (10 ml.) and potassium carbonate (0.732 g.) at 0° to 5° C. over 2 minutes, and the solution was stirred at room temperature for 2.5 hours. After ethyl acetate and water were added to the resultant solution, the solution was extracted with ethyl acetate. The remaining aqueous layer was extracted again with ethyl acetate. The ethyl acetate extract solution was washed with a saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to column chromatography on silica gel (30 g.) and eluted with a mixture of chloroform and ethyl acetate. The eluate was concentrated under reduced pressure to give 4-nitrobenzyl 7-[2-(2-formamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate (syn isomer, 0.12 g.), mp 224° C. (dec.).

후처리

  1. extractionthe solution was extracted with ethyl acetate
  2. extractionThe remaining aqueous layer was extracted again with ethyl acetate
  3. extractionThe ethyl acetate extract solution
  4. washwas washed with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washeluted with a mixture of chloroform and ethyl acetate
  8. concentrationThe eluate was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-0e1c696907544ded8d221502343911e7
출처 데이터셋
uspto-grants-1986_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04604456

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