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Ethyl Acetate → HCID 22493882、化合物

HRID 1816601
ノート
印刷プレビュー

反応式

HRID 1816601 の反応式
Br[C:2]1[CH:3]=[C:4]([CH2:19][CH:20]([O:26][CH:27]([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:5]=[C:6]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]=1[O:8][CH3:9].[C-:30]#[N:31].[Na+].C(OCC)(=O)C>C(#N)CC.[Cu](I)I>[C:30]([C:2]1[CH:3]=[C:4]([CH2:19][CH:20]([O:26][CH:27]([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH:5]=[C:6]([CH2:10][NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[C:7]=1[O:8][CH3:9])#[N:31]
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 ethyl 3-(3-bromo-5-[(tertiary butoxycarbonyl)amino]methyl-4-methoxyphenyl)-2-isopropoxypropionate was dissolved in 5 ml propionitrile, and 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 a nitrogen atmosphere. The reaction mixture was cooled to room temperature, ethyl acetate was added thereto and filtered through Celite. The filtrate was evapoarated and the residue was purified by silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (4:1), 586 mg of ethyl 3-(3-cyano-5-[(tertiary butoxycarbonyl)amino]methyl-4-methoxyphenyl)-2-isopropoxypropionate was obtained.

後処理

  1. temperatureby heating
  2. temperatureunder reflux overnight in a nitrogen atmosphere
  3. filtrationfiltered through Celite
  4. customthe residue was purified by silica gel column chromatography
  5. washfrom fractions eluted with hexane-ethyl acetate (4:1)

出典と根拠

ORDレコード
ord-410550954f1346e8813d297c53da5af7
出典データセット
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06884821B1

反応ノート

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