반응 #47491

반응 방정식

(E)-4-bromo-3-(2-methylsulfanyl-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-methylsulfanyl-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester

수율 12.8%

용매

N,N-dimethylformamide

반응 조건

후처리

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

실험 절차

To a stirred solution of (S)-2-amino-3-cyclohexyl-propionic acid methyl ester (1.10 g, 0.006 mol) in N,N-dimethylformamide (10 mL) was added N,N-diisopropylethylamine (3.51 g, 0.027 mol) slowly at room temperature, under nitrogen. The resulting mixture was stirred for 5 min and then treated with (E)-4-bromo-3-(2-methylsulfanyl-phenoxy)-but-2-enoic acid ethyl ester (1.80 g, 0.005 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-methylsulfanyl-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (250 mg, 11%) as a yellow oil.

출처