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Ethyl Acetate → HCID 22493882, 화합물

HRID 1816601
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HRID 1816601 반응식
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]
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 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.

후처리

  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)

출처 및 근거

ORD 기록
ord-410550954f1346e8813d297c53da5af7
출처 데이터셋
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06884821B1

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