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Ethyl Acetate → N-(3-chloro-4-cyanophenyl)-4-fluorophenylalanine

HRID 1967322
ノート
印刷プレビュー

反応式

HRID 1967322 の反応式
[Cl:1][C:2]1[CH:9]=[C:8](F)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F:11][C:12]1[CH:23]=[CH:22][C:15]([CH2:16][C@@H:17]([C:19]([OH:21])=[O:20])[NH2:18])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OCC)(=O)C>CS(C)=O>[Cl:1][C:2]1[CH:9]=[C:8]([NH:18][C@H:17]([C:19]([OH:21])=[O:20])[CH2:16][C:15]2[CH:14]=[CH:13][C:12]([F:11])=[CH:23][CH:22]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 1090002-Chloro-4-fluorobenzonitrileHCID 7163124-fluoro-L-phenylalanine

生成物 1

HCID 67105225N-(3-chloro-4-cyanophenyl)-4-fluorophenylalanine収率 100.1%

試薬・触媒・溶媒 1

HCID 679
Dimethyl Sulfoxide
溶媒

反応条件

温度
90 °C

実験手順

To a solution of 2-chloro-4-fluorobenzonitrile (1.8 g) in dimethyl sulfoxide (30 mL) were added 4-fluorophenylalanine (2.54 g) and cesium carbonate (4.90 g), and the mixture was stirred at 90° C. overnight. After allowing to room temperature, ethyl acetate was added, and the mixture was extracted twice with saturated aqueous sodium hydrogen carbonate solution. The aqueous layers were combined, and acidified with citric acid, and the mixture was extracted twice with ethyl acetate. The organic layers were combined, washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound as a brown oil (yield: 3.69 g, 100%).

後処理

  1. customAfter allowing to room temperature
  2. extractionthe mixture was extracted twice with saturated aqueous sodium hydrogen carbonate solution
  3. extractionthe mixture was extracted twice with ethyl acetate
  4. washwashed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-1c3b502b23944b5ab5ce0b2610de398a
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08420694B2

反応ノート

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