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N-[2-(t-Butyldimethylsilanyloxy)-ethoxy]-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-5-vinyl-benzamide → N-[2-(t-butyldimethylsilanyloxy)-ethoxy]-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-5-formyl-benzamide

HRID 661716
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인쇄 미리보기

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HRID 661716 반응식
[Si:1]([O:8][CH2:9][CH2:10][O:11][NH:12][C:13](=[O:33])[C:14]1[CH:19]=[C:18]([CH:20]=C)[C:17]([F:22])=[C:16]([F:23])[C:15]=1[NH:24][C:25]1[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=1[F:32])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].I([O-])(=O)(=O)=[O:35].[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[Si:1]([O:8][CH2:9][CH2:10][O:11][NH:12][C:13](=[O:33])[C:14]1[CH:19]=[C:18]([CH:20]=[O:35])[C:17]([F:22])=[C:16]([F:23])[C:15]=1[NH:24][C:25]1[CH:30]=[CH:29][C:28]([I:31])=[CH:27][C:26]=1[F:32])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]
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참가 물질

6

반응물 2

HCID 23132384N-[2-(t-Butyldimethylsilanyloxy)-ethoxy]-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-5-vinyl-benzamideHCID 23667635Sodium periodate

생성물 1

HCID 23132329N-[2-(t-butyldimethylsilanyloxy)-ethoxy]-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-5-formyl-benzamide수율 51%

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매
HCID 962
Water
용매
HCID 8028Tetrahydrofuran용매

실험 절차

N-[2-(t-Butyldimethylsilanyloxy)-ethoxy]-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-5-vinyl-benzamide (6.35 g, 10.7 mmol) prepared in Process A was dissolved in a mixed solvent of THF (100 ml) and water (30 ml). Aqueous solution of osmium tetroxide (0.1 mM, 2 ml, 0.2 mmol), and sodium metaperiodate (9.0 g, 42.1 mmol) were added at 10° C., and the mixture was stirred at room temperature for 17 hours. Insoluble material was removed through a celite column, and the solution was extracted with ethyl acetate. The extract was washed successively with water and saturated brine, the organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (300 g, n-hexane/ethyl acetate (5:1)) to give N-[2-(t-butyldimethylsilanyloxy)-ethoxy]-3,4-difluoro-2-(2-fluoro-4-iodophenylamino)-5-formyl-benzamide (3.24 g, 51%) as a brown solid.

후처리

  1. customInsoluble material was removed through a celite column
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe extract was washed successively with water and saturated brine
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was purified by silica gel chromatography (300 g, n-hexane/ethyl acetate (5:1))

출처 및 근거

ORD 기록
ord-77f8f3dab5dc432c88308767cb2f8854
출처 데이터셋
uspto-grants-2011_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08084645B2

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