Bromide ion → HCID 18612902, 화합물

HRID 1264615노트

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HRID 1264615 반응식
Br[CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[N+:10]([O-:12])=[O:11].[CH2:13]([O:17][C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH:27][CH:28]([CH2:33][OH:34])[C:29]([O:31][CH3:32])=[O:30])(=[O:26])=[O:25])=[CH:20][CH:19]=1)C#CC.[H-].[Na+].[Br-]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[F:9][C:7]1[CH:6]=[CH:5][C:4]([N+:10]([O-:12])=[O:11])=[C:3]([CH:8]=1)[CH2:2][N:27]([S:24]([C:21]1[CH:20]=[CH:19][C:18]([O:17][CH3:13])=[CH:23][CH:22]=1)(=[O:26])=[O:25])[CH:28]([CH2:33][OH:34])[C:29]([O:31][CH3:32])=[O:30]

참가 물질

7

반응물 4

HCID 259Bromide ionHCID 24758Sodium hydrideHCID 105616432-(Bromomethyl)-4-fluoro-1-nitrobenzeneHCID 12016494N-[[4-(2-Butyn-1-yloxy)phenyl]sulfonyl]serine methyl ester

생성물 1

HCID 18612902HCID 18612902, 화합물수율 84.1%

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

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온도
0 °C

실험 절차

To a solution was of 2-(bromomethyl)-4-fluoro-1-nitrobenzene (1.3 g, 5.56 mmol) at 0° C. was added tetrabutylammonium iodide (2.05 g, 5.56 mmol). The solution was stirred at 0° C. for 1.5 hours. In a separate flask, methyl 2-({[4-(2-butynyloxy)phenyl]sulfonyl}amino)-3-hydroxypropanoate (1.73 g, 5.05 mmol) was dissolved in dimethylformamide and cooled to 0° C. Sodium hydride (0.21 g, 5.56 mmol, 60% dispersion in oil) was added and the reaction was allowed to stir at 0° C. for 0.5 hours at which time the solution of the bromide was added. The reaction was stirred overnight and then quenched with water. The mixture was extracted twice with ethyl acetate, washed with brine, dried over Na2SO4, concentrated in vacuo and chromatographed using 1.5:1 hexane:ethyl acetate as eluant to provide 1.88 g (77%) of the desired product as a white solid. mp 83-88° C. Anal Calc'd for C21H21N2O8FS: C, 52.50; H, 4.41; N, 5.83. Found: C, 52.44; H, 4.76; N, 5.56.

후처리

  1. temperaturecooled to 0° C
  2. additionwas added
  3. stirringThe reaction was stirred overnight
  4. customquenched with water
  5. extractionThe mixture was extracted twice with ethyl acetate
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customchromatographed

출처 및 근거

ORD 기록
ord-aa94157ae0814b4e88941edb88c54668
출처 데이터셋
uspto-grants-2003_04
특허 번호
US06544984B1

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