تفاعل #47496

معادلة التفاعل

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

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

N,N-diisopropylethylamine

→

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

المردود 29.3%

المذيبات

N,N-dimethylformamide

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe reaction mixture was heated at 110° C.-120° C. for 16 h
2. 2
   استخلاصthe resulting mixture was extracted with ethyl acetate
3. 3
   غسيلThe combined organic layers were washed with a saturated aqueous sodium chloride solution
4. 4
   تجفيفdried over sodium sulfate
5. 5
   تركيزconcentrated in vacuo
6. 6
   أخرىPurification by flash column chromatography (silica gel (100-200 mesh))

الإجراء التجريبي

To a stirred solution of (S)-2-amino-3-cyclohexyl-propionic acid methyl ester (960 mg, 0.005 mol) in N,N-dimethylformamide (8 mL) was added N,N-diisopropylethylamine (3.00 g, 0.023 mol) slowly at room temperature, under nitrogen. The resulting mixture was stirred for 5 min and then treated with (E)-4-bromo-3-(2-t-butyl-phenoxy)-but-2-enoic acid ethyl ester (1.60 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)-2-[4-(2-t-butyl-phenoxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-3-cyclohexyl-propionic acid methyl ester (585 mg, 28%) as yellow oil.

المصدر