Triethylamine → Ethyl 2-[4-methoxy-3-({[4-(trifluoromethyl)benzoyl]amino}methyl)benzyl]butanoate

HRID 1816562ノート

反応式

HRID 1816562 の反応式
[NH2:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[CH2:6][CH:7]([CH2:13][CH3:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9].[F:20][C:21]([F:32])([F:31])[C:22]1[CH:30]=[CH:29][C:25]([C:26](O)=[O:27])=[CH:24][CH:23]=1.C(P(=O)(OCC)OCC)#N.C(N(CC)CC)C>CN(C)C=O>[CH3:19][O:18][C:17]1[CH:16]=[CH:15][C:5]([CH2:6][CH:7]([CH2:13][CH3:14])[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:4][C:3]=1[CH2:2][NH:1][C:26](=[O:27])[C:25]1[CH:29]=[CH:30][C:22]([C:21]([F:20])([F:31])[F:32])=[CH:23][CH:24]=1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 99664-(Trifluoromethyl)benzoic acidHCID 76257Diethyl cyanophosphonateHCID 11108255Ethyl 2-[3-(aminomethyl)-4-methoxybenzyl]butanoate

生成物 1

HCID 11004633Ethyl 2-[4-methoxy-3-({[4-(trifluoromethyl)benzoyl]amino}methyl)benzyl]butanoate収率 89.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

0.40 g of ethyl 2-[3-(aminomethyl)-4-methoxybenzyl]butanoate and 0.29 g of 4-(trifluoromethyl)benzoic acid were dissolved in 5 ml N,N-dimethylformamide, and 0.24 ml diethyl cyanophosphonate and 0.21 ml triethylamine were added under ice-cooling. After stirring the reaction mixture at room temperature for 16 hours, the mixture 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 evapoarated. The residue was subjected to silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (3:1), 0.59 g of ethyl 2-[4-methoxy-3-({[4-(trifluoromethyl)benzoyl]amino}methyl)benzyl]butanoate 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. washfrom fractions eluted with hexane-ethyl acetate (3:1)

出典と根拠

ORDレコード
ord-022d530a45b94d1181320cfbd4fb305c
出典データセット
uspto-grants-2005_04
特許番号
US06884821B1

反応ノート

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