Water → (e)-Methyl 4-(benzyl(2-(tritylamino)ethyl)amino)but-2-enoate

HRID 80492

反応式

HRID 80492 の反応式
[CH2:1]([NH:8][CH2:9][CH2:10][NH:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:32]/[CH:33]=[CH:34]/[C:35]([O:37][CH3:38])=[O:36].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH2:1]([N:8]([CH2:9][CH2:10][NH:11][C:12]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:32]/[CH:33]=[CH:34]/[C:35]([O:37][CH3:38])=[O:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 53691752-Butenoic acid, 4-bromo-, methyl esterHCID 11784164N1-benzyl-N2-tritylethane-1,2-diamine

生成物 1

HCID 67247765(e)-Methyl 4-(benzyl(2-(tritylamino)ethyl)amino)but-2-enoate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

To a solution of Example 12A (128 g, 326 mmol) in acetonitrile (652 mL) was added (E)-methyl 4-bromobut-2-enoate (38.4 mL, 326 mmol) and potassium carbonate (90 g, 652 mmol), and the mixture was heated at 50° C. for 17 hours. A small amount of water was added, and the mixture was decanted into a separatory funnel. The solid left behind was washed three times with ethyl acetate, and the ethyl acetate washings were added to the separatory funnel followed by more water. The layers were separated and the organic layer was concentrated, then dissolved in dichloromethane and loaded onto a silica gel column packed in hexanes. The product was eluted with 15% ethyl acetate/hexanes to afford the title compound. 1H NMR (500 MHz, DMSO-d6) δ ppm 7.38 (d, J=7.3 Hz, 5H), 7.31-7.12 (m, 15H), 6.83 (dt, J=5.6 Hz, 15.7 Hz, 1H), 6.07 (d, J=15.7 Hz, 1H), 3.67 (s, 3H), 3.42 (s, 2H), 3.05 (d, J=4.4 Hz, 2H), 2.58-2.49 (m, 2H), 2.11 (dd, J=6.2 Hz, 12.9 Hz, 2H).

後処理

  1. customthe mixture was decanted into a separatory funnel
  2. waitThe solid left behind
  3. washwas washed three times with ethyl acetate
  4. additionthe ethyl acetate washings were added to the separatory funnel
  5. customThe layers were separated
  6. concentrationthe organic layer was concentrated
  7. dissolutiondissolved in dichloromethane
  8. washThe product was eluted with 15% ethyl acetate/hexanes

出典と根拠

ORDレコード
ord-8f41388790874c06901466a37659dd7e
出典データセット
uspto-grants-2014_09
特許番号
US08846663B2

関連ノート

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