Ethyl bromoacetate → (s)-[But-3-enyl-(1-phenyl-ethyl)-amino]-acetic acid ethyl ester

HRID 77265

反応式

HRID 77265 の反応式
[CH2:1]([NH:5][C@H:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:7])[CH2:2][CH:3]=[CH2:4].C([O-])([O-])=O.[K+].[K+].[CH2:20]([O:22][C:23](=[O:26])[CH2:24]Br)[CH3:21]>CN(C=O)C.CCOCC>[CH2:20]([O:22][C:23](=[O:26])[CH2:24][N:5]([CH2:1][CH2:2][CH:3]=[CH2:4])[C@H:6]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH3:7])[CH3:21]

参加物

6

反応物 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 10559173But-3-enyl-((S)-1-phenyl-ethyl)-amine

生成物 1

HCID 10956339(s)-[But-3-enyl-(1-phenyl-ethyl)-amino]-acetic acid ethyl ester収率 94.5%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

To a solution of But-3-enyl-((S)-1-phenyl-ethyl)-amine (6.37 g, 36.4 mmol) in 150 mL of DMF at 0° C. is added K2CO3 (10.0 g, 72.8 mmol) in small portions. After stirring at 0° C. for 10 min, ethylbromoacetate (8.35 g, 54.6 mmol) is added slowly. The reaction mixture, a white suspension, is stirred at r.t. overnight/16 hrs. The solution is diluted with 200 mL of ether, and washed with 3×100 ml of water. The crude product is purified by chromatography (hexane/CH2Cl2: 50/50) to give a pale liquid (8.5 g, 94.5%).

後処理

  1. stirringThe reaction mixture, a white suspension, is stirred at r.t. overnight/16 hrs
  2. washwashed with 3×100 ml of water
  3. customThe crude product is purified by chromatography (hexane/CH2Cl2: 50/50)

出典と根拠

ORDレコード
ord-ee12a1da23954a22838b09c77b9a9393
出典データセット
uspto-grants-2014_09
特許番号
US08841067B2

関連ノート

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