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Ethyl Acetate → HCID 22493882、化合物

HRID 1296209
ノート
印刷プレビュー

反応式

HRID 1296209 の反応式
[CH2:1]([O:3][C:4](=[O:29])[CH:5]([O:25][CH:26]([CH3:28])[CH3:27])[CH2:6][C:7]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([O:22][CH3:23])=[C:9](Br)[CH:8]=1)[CH3:2].[C-:30]#[N:31].[Na+].C(OCC)(=O)C>C(#N)CC.[Cu](I)I>[CH2:1]([O:3][C:4](=[O:29])[CH:5]([O:25][CH:26]([CH3:28])[CH3:27])[CH2:6][C:7]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([O:22][CH3:23])=[C:9]([C:30]#[N:31])[CH:8]=1)[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 22494028HCID 22494028、化合物

生成物 1

HCID 22493882HCID 22493882、化合物収率 75.5%

試薬・触媒・溶媒 2

HCID 83717Copper iodide触媒HCID 7854Propionitrile溶媒

実験手順

876 mg of 3(3-bromo-5-[(t-butoxycarbonyl)amino]methyl-4-methoxyphenyl)-2-isopropoxypropionic acid ethyl ester was dissolved in 5 ml of propionitrile. 182 mg of sodium cyanide, 214 mg of tetrakistriphenylphosphine palladium and 70 mg of copper iodide were added, followed by heating under reflux overnight in nitrogen atmosphere. The reaction mixture was cooled down to room temperature, and ethyl acetate was added thereto. The solution was filtered through Celite, and the filtrate was evaporated. The residue was purified by silica gel column chromatography, to give 586 mg of 3-(3-cyano-5-[(t-butoxycarbonyl)amino]methyl-4-methoxyphenyl)-2-isopropoxypropionic acid ethyl ester from fractions eluted with hexane-ethyl acetate (4:1).

後処理

  1. temperatureby heating
  2. temperatureunder reflux overnight in nitrogen atmosphere
  3. filtrationThe solution was filtered through Celite
  4. customthe filtrate was evaporated
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-94fa3ff66b3942bfba1ad8b92e2797a4
出典データセット
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07244861B2

反応ノート

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