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Triethylamine → ethyl (Z)-2-isopropoxy-3-[4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)phenyl]-2-propenoate

HRID 1816559
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HRID 1816559 반응식
[CH2:1]([O:3][C:4](=[O:22])/[C:5](/[O:18][CH:19]([CH3:21])[CH3:20])=[CH:6]/[C:7]1[CH:8]=[CH:9][C:10]([O:16][CH3:17])=[C:11]([CH:15]=1)[C:12]([OH:14])=O)[CH3:2].[F:23][C:24]([F:34])([F:33])[C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O>[CH:19]([O:18]/[C:5](=[CH:6]\[C:7]1[CH:8]=[CH:9][C:10]([O:16][CH3:17])=[C:11]([C:12]([NH:30][CH2:29][C:28]2[CH:27]=[CH:26][C:25]([C:24]([F:23])([F:33])[F:34])=[CH:32][CH:31]=2)=[O:14])[CH:15]=1)/[C:4]([O:3][CH2:1][CH3:2])=[O:22])([CH3:21])[CH3:20]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 768044-(Trifluoromethyl)benzylamineHCID 599979455-[(Z)-3-ethoxy-2-isopropoxy-3-oxo-1-propenyl]-2-methoxybenzoic acid

생성물 1

HCID 86759678ethyl (Z)-2-isopropoxy-3-[4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)phenyl]-2-propenoate수율 78.5%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

65 mg of 5-[(Z)-3-ethoxy-2-isopropoxy-3-oxo-1-propenyl]-2-methoxybenzoic acid and 37 mg of 4-(trifluoromethyl)benzylamine were dissolved in 1 ml N,N-dimethylformamide, and 33 μl diethyl cyanophosphonate and 30 μl triethylamine were added under ice-cooling. After stirring the reaction mixture at room temperature for 16 hours, it was poured into ice-water and extracted with ethyl acetate. The organic layer was successively washed with 1N hydrochloric acid and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (5:1), 77 mg of ethyl (Z)-2-isopropoxy-3-[4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)phenyl]-2-propenoate was obtained.

후처리

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was successively washed with 1N hydrochloric acid and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated
  6. washfrom fractions eluted with hexane-ethyl acetate (5:1)

출처 및 근거

ORD 기록
ord-ecba6607c52d4d5c8dc47a9abb0535de
출처 데이터셋
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06884821B1

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