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

HRID 80492

반응식

HRID 80492 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
50 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-8f41388790874c06901466a37659dd7e
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846663B2

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