Реакция #47480

Уравнение реакции

4-bromo-3-(2,3-dichloro-phenoxy)-but-2-enoic acid ethyl ester

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

N,N-diisopropylethylamine

→

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

Выход 17.0%

Растворители

N,N-dimethylformamide

Условия реакции

Обработка

1. 1
   Температураthe reaction mixture was heated at 110° C.-120° C. for 16 h
2. 2
   Экстракцияthe resulting mixture was extracted with ethyl acetate
3. 3
   ПромывкаThe combined organic layers were washed with a saturated aqueous sodium chloride solution
4. 4
   Сушкаdried over sodium sulfate
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   ДругоеPurification

Методика

To a stirred solution of (S)-2-amino-3-cyclohexyl-propionic acid methyl ester (1.15 g, 0.062 mol) in N,N-dimethylformamide (5 mL) was added N,N-diisopropylethylamine (3.63 g, 0.282 mol) slowly at room temperature, under nitrogen. The resulting mixture was stirred for 5 min and then treated with 4-bromo-3-(2,3-dichloro-phenoxy)-but-2-enoic acid ethyl ester (2.0 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 using flash column chromatography (silica gel (100-200 mesh)) afforded (S)-3-cyclohexyl-2-[4-(2,3-dichloro-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (0.40 g, 17%) as a yellow oil.

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