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

HRID 1035272Notes

Reaction equation

HRID 1035272 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-914fc010565c47049c6bebb47e9feb65
Source dataset
uspto-grants-2013_10
Patent number
US08546377B2

Reaction notes

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