Réaction #531881

Équation de réaction

triethylamine

ethyl 3-chloro-3-(3-chloro-4-methyl-2-thienyl)-2-cyanoacrylate

N-methyl-L-alaninamide hydrochloride

→

ethyl (2Z)-3-(3-chloro-4-methyl-2-thienyl)-2-cyano-3-{[(2R)-1-(methylamino)-1-oxopropan-2-yl]amino}acrylate

Rendement 60.4%

Solvants

acetonitrile

Conditions de réaction

Traitement

1. 1
   AutreThe reaction was microwaved
2. 2
   Autre(130° C., 300 s, fixed hold, high absorption)
3. 3
   Autrethe solvent evaporated
4. 4
   AutreThe residual oil was triturated in ethyl acetate
5. 5
   Autrethe white solid removed by filtration
6. 6
   ConcentrationAfter concentration under vacuum

Mode opératoire

To a solution of ethyl 3-chloro-3-(3-chloro-4-methyl-2-thienyl)-2-cyanoacrylate (0.351 g, 1.21 mmol, 1 eq.) in 3 ml of acetonitrile was added N-methyl-L-alaninamide hydrochloride (0.201 g, 1.45 mmol, 1.2 eq.) followed by triethylamine (TEA) (0.490 g, 4.84 mmol, 4 eq.). The reaction was microwaved (130° C., 300 s, fixed hold, high absorption) and the solvent evaporated. The residual oil was triturated in ethyl acetate and the white solid removed by filtration. After concentration under vacuum, the residual oil was subjected to column chromatography to give ethyl (2Z)-3-(3-chloro-4-methyl-2-thienyl)-2-cyano-3-{[(2R)-1-(methylamino)-1-oxopropan-2-yl]amino}acrylate (0.26 g, 57% yield) as a mixture of atropoisomers.

Source