Réaction #47486

Équation de réaction

(E)-4-bromo-3-(2-isopropoxy-phenoxy)-but-2-enoic acid ethyl ester

(S)-2-amino-3-cyclohexyl-propionic acid methyl ester

N,N-diisopropylethylamine

→

(S)-3-cyclohexyl-2-[4-(2-isopropoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester

Rendement 29.9%

Solvants

N,N-dimethylformamide

Conditions de réaction

Traitement

1. 1
   Températurethe reaction mixture was heated at 110° C.-120° C. for 16 h
2. 2
   Extractionthe resulting mixture was extracted with ethyl acetate
3. 3
   LavageThe combined organic layers were washed with a saturated aqueous sodium chloride solution
4. 4
   Séchagedried over sodium sulfate
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutrePurification by flash column chromatography (silica gel (100-200 mesh))

Mode opératoire

To a stirred solution of (S)-2-amino-3-cyclohexyl-propionic acid methyl ester (1.20 g, 0.006 mol) in N,N-dimethylformamide (8 mL) was added N,N-diisopropylethylamine (3.76 g, 0.029 mol) slowly at room temperature, under nitrogen. The resulting mixture was stirred for 5 min and then treated with (E)-4-bromo-3-(2-isopropoxy-phenoxy)-but-2-enoic acid ethyl ester (2.00 g, 0.006 mol) and the reaction mixture was heated at 110° C.-120° C. for 16 h. After this time, ice water was added and the resulting mixture was extracted with ethyl acetate. The combined organic layers were washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and concentrated in vacuo. Purification by flash column chromatography (silica gel (100-200 mesh)) afforded (S)-3-cyclohexyl-2-[4-(2-isopropoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (0.720 g, 28%) as a yellow oil.

Source