Reaktion #531881

Reaktionsgleichung

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

Ausbeute 60.4%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle