Bromide ion → HCID 18612902、化合物

HRID 1264615ノート

反応式

HRID 1264615 の反応式
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]

参加物

7

反応物 4

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

生成物 1

HCID 18612902HCID 18612902、化合物収率 84.1%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-aa94157ae0814b4e88941edb88c54668
出典データセット
uspto-grants-2003_04
特許番号
US06544984B1

反応ノート

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