تفاعل #927122

معادلة التفاعل

N,N'-dicyclohexylcarbodiimide

N-(4-methoxybenzoyl)-phenylalanine

methyl tyrosinate hydrochloride

→

methyl N-(4-methoxybenzoyl)-phenylalanyltyrosinate

المردود 74.0%

المذيبات

chloroform tetrahydrofuran

—

mixture

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was cooled with ice
2. 2
   workup.WAITto sit 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

الإجراء التجريبي

In 500 ml of a mixture of chloroform-tetrahydrofuran (2:1), were dissolved 29.9 g of N-(4-methoxybenzoyl)-phenylalanine, 23.2 g of methyl tyrosinate hydrochloride, 10.1 g of trethylamine and 11.6 g of H-hydroxysuccinimide and the mixture was cooled with ice. To the cold solution was added 20.6 g of N,N'-dicyclohexylcarbodiimide. The mixture was stirred for two hours and then allowed to sit at room temperature overnight. The precipitates were removed by filtration and the filtrate was concentrated. The residue was extracted with ethyl acetate. 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 to give 35 g of methyl N-(4-methoxybenzoyl)-phenylalanyltyrosinate with a mp. 195°-197° C in a yield of 74%. Analysis, calculated for C27H28O6N2C 68.05, H 5.92, N 5.88, found C 67.84, H 5.92, N 5.57.

المصدر