Triethylamine → 3-(4-t-butylphenyl)-N-(4-methanesulfonylamino-3-vinylbenzyl)acryl Amide

HRID 2358395Notes

Reaction equation

HRID 2358395 reaction equation
[NH2:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:5]([CH:14]=[CH2:15])[CH:4]=1.[C:16]([C:20]1[CH:25]=[CH:24][C:23]([CH:26]=[CH:27][C:28](O)=[O:29])=[CH:22][CH:21]=1)([CH3:19])([CH3:18])[CH3:17].C(N(CC)CC)C.C(OP(C#N)(=O)OCC)C>CN(C=O)C>[C:16]([C:20]1[CH:21]=[CH:22][C:23]([CH:26]=[CH:27][C:28]([NH:1][CH2:2][C:3]2[CH:8]=[CH:7][C:6]([NH:9][S:10]([CH3:13])(=[O:12])=[O:11])=[C:5]([CH:14]=[CH2:15])[CH:4]=2)=[O:29])=[CH:24][CH:25]=1)([CH3:19])([CH3:17])[CH3:18]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 7248384-Tert-butylcinnamic acidHCID 57665523N-(4-aminomethyl-2-vinylphenyl)methanesulfonamide

Product 1

HCID 684536133-(4-t-butylphenyl)-N-(4-methanesulfonylamino-3-vinylbenzyl)acryl AmideYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A dried 25 ml two-neck round bottom flask was filled with argon gas and the solution of N-(4-aminomethyl-2-vinyl-phenyl)-methanesulfonamide (51 mg, 0.23 mmol) and 3-(4-t-butyl-phenyl)-acrylic acid (1.2 eq, 0.27 mmol, 55.26 mg) in DMF was put into the flask. To the solution were added triethylamine (2 eq, 0.46 mmol, 64.12 mg) and diethylcyanophosphonate (1.2 eq, 0.27 mmol, 41.88 μl) and stirred for 12 hours. After confirming the completion of the reaction with TLC, the reaction solution was extracted with methylenechloride, washed with water and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The obtained liquid was column-chromatographed (n-hexane/ethyl acetate=1/1) to yield a white solid (48.4 mg, 43.37%).

Workup

  1. additionA dried 25 ml two-neck round bottom flask was filled with argon gas
  2. customthe completion of the reaction with TLC
  3. extractionthe reaction solution was extracted with methylenechloride
  4. washwashed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe obtained liquid was column-chromatographed (n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-a33724fc04d84833b7154840d018cfe6
Source dataset
uspto-grants-2010_07
Patent number
US07763657B2

Reaction notes

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