Triethylamine → cyanomethyl 2-(N-methylpent-4-enamido)acetate

HRID 1482381Notes

Reaction equation

HRID 1482381 reaction equation
Cl.[CH3:2][NH:3][CH2:4][C:5]([O:7][CH2:8][C:9]#[N:10])=[O:6].C(N(CC)CC)C.[C:18](Cl)(=[O:23])[CH2:19][CH2:20][CH:21]=[CH2:22]>ClCCl>[CH3:2][N:3]([CH2:4][C:5]([O:7][CH2:8][C:9]#[N:10])=[O:6])[C:18](=[O:23])[CH2:19][CH2:20][CH:21]=[CH2:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 42284934-Pentenoyl chlorideHCID 117736071Cyanomethyl 2-(methylamino)acetate hydrochloride

Product 1

HCID 89668754cyanomethyl 2-(N-methylpent-4-enamido)acetateYield 88.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyanomethyl 2-(methylamino)acetate hydrochloride (Compound SP703) (3.00 g, 18.3 mmol) and triethylamine (6.34 ml, 45.5 mmol) were dissolved in dichloromethane (30 ml) under a nitrogen atmosphere, and pent-4-enoyl chloride (2.60 g, 22.0 mmol) was added dropwise at 0° C. The reaction solution was stirred at room temperature for 2 hours and 30 minutes and then concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate, and the solid was removed by filtration. The solution was concentrated under reduced pressure and purified by column chromatography (ethyl acetate:petroleum ether=1:10→2:7) to afford cyanomethyl 2-(N-methylpent-4-enamido)acetate (Compound SP704) (3.40 g, 88%).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe resulting residue was dissolved in ethyl acetate
  3. customthe solid was removed by filtration
  4. concentrationThe solution was concentrated under reduced pressure
  5. custompurified by column chromatography (ethyl acetate:petroleum ether=1:10→2:7)

Sources & evidence

ORD record
ord-d6bfa8d7fc1d422b84a561755ca54dda
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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