تفاعل #927121

معادلة التفاعل

N,N'-dicyclohexylcarbodiimide

N-benzoylphenylalanine

methyl tyrosinate hydrochloride

N-hydroxysuccinimide

→

methyl N-benzoylphenylalanyltyrosinate

المردود 74.0%

المذيبات

chloroform tetrahydrofuran

triethylamine

—

mixture

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe solution was cooled with ice
2. 2
   workup.WAITto stand at room temperature overnight
3. 3
   أخرىThe precipitates were removed by filtration
4. 4
   تركيزthe filtrate was concentrated
5. 5
   استخلاصThe residue was extracted with ethyl acetate
6. 6
   غسيلthe extract was washed with 2% hydrochloric acid, 4% sodium bicarbonate and water
7. 7
   أخرىdried
8. 8
   تركيزconcentrated to dryness
9. 9
   أخرىThe residue was crystallized from ethyl acetate-petroleum ether

الإجراء التجريبي

In 100 ml of a mixture of chloroform-tetrahydrofuran (2:1), were dissolved 5.39 g of N-benzoylphenylalanine, 4.64 g of methyl tyrosinate hydrochloride, 2.02 g of triethylamine and 2.30 g of N-hydroxysuccinimide and the solution was cooled with ice. To the cold solution, 4.12 g of N,N'-dicyclohexylcarbodiimide was added. The mixture was stirred for three hours, then allowed to stand at room temperature overnight. The precipitates were removed by filtration and the filtrate was concentrated. The residue was extracted with ethyl acetate and the extract was washed with 2% hydrochloric acid, 4% sodium bicarbonate and water, then dried and concentrated to dryness. The residue was crystallized from ethyl acetate-petroleum ether to give 6.6 g of methyl N-benzoylphenylalanyltyrosinate with a mp. 188°-190° C in a yield of 74%. Analysis, calculated for C26H26O5N2C 69.94, H 5.87, N 6.27, found C 69.56, H 6.01, N 6.39.

المصدر