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Ethyl Acetate → HCID 22493882, 화합물

HRID 1296209
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HRID 1296209 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 8857Ethyl AcetateHCID 8929Sodium CyanideHCID 22494028HCID 22494028, 화합물

생성물 1

HCID 22493882HCID 22493882, 화합물수율 75.5%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 7854Propionitrile용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-94fa3ff66b3942bfba1ad8b92e2797a4
출처 데이터셋
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07244861B2

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