Реакция #2275691

Уравнение реакции

ethylacetate

acetic acid {3-chlorocarbonyl-5-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-methyl ester

5-[Acetyl-(3-amino-2-hydroxy-propyl)-amino]-N-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-N′-(dimethyl-[1,3]dioxolan-4-ylmethyl)-2,4,6-triiodo-isophthalamide

triethylamine

→

acetic acid {3-[3-(acetyl-{3,5-bis-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenyl}-amino)-2-hydroxy-propylcarbamoyl]-5-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-methyl ester

Выход 33.0%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Промывкаwashed with water
2. 2
   ДругоеThe organics were collected
3. 3
   Сушкаdried over MgSO4
4. 4
   Фильтрацияfiltered
5. 5
   Другоеevaporated to dryness
6. 6
   ДругоеThe product was purified by silica column chromatography
7. 7
   Промывкаeluting with ethylacetate/MeOH

Методика

To a solution of 5-[Acetyl-(3-amino-2-hydroxy-propyl)-amino]-N-(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-N′-(dimethyl-[1,3]dioxolan-4-ylmethyl)-2,4,6-triiodo-isophthalamide (2.0 g, 2 mmol) in DMF (4 mL) were added triethylamine (0.45 g, 4 mmol, 2 eq) followed by acetic acid {3-chlorocarbonyl-5-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-methyl ester (1.85 g, 2 mmol, 1 eq). The reaction mixture was stirred at room temperature overnight under nitrogen. The mixture was diluted with ethylacetate and washed with water. The organics were collected, dried over MgSO4, filtered and evaporated to dryness. The product was purified by silica column chromatography eluting with ethylacetate/MeOH to give acetic acid {3-[3-(acetyl-{3,5-bis-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenyl}-amino)-2-hydroxy-propylcarbamoyl]-5-[(2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-methyl ester (725 μmol, Yield=33%).

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