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

HRID 1816559
ノート
印刷プレビュー

反応式

HRID 1816559 の反応式
[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]
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 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ecba6607c52d4d5c8dc47a9abb0535de
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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