Reacción #47549

Ecuación de reacción

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

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

N,N-diisopropylethylamine

→

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

Rendimiento 50.0%

Disolventes

N,N-dimethylformamide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

To a stirred solution of (S)-2-amino-3-cyclohexyl-propionic acid methyl ester (1.20 g, 0.006 mol) in N,N-dimethylformamide (10 mL) was added N,N-diisopropylethylamine (4.06 g, 0.031 mol) slowly at room temperature, under nitrogen. The resulting mixture was stirred for 5 min and then treated with (E)-4-bromo-3-(3-methoxy-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-(3-methoxy-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (1.12 g, 46%) as a yellow oil.

Fuente