Réaction #2275691

Équation de réaction

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

Rendement 33.0%

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   Lavagewashed with water
2. 2
   AutreThe organics were collected
3. 3
   Séchagedried over MgSO4
4. 4
   Filtrationfiltered
5. 5
   Autreevaporated to dryness
6. 6
   AutreThe product was purified by silica column chromatography
7. 7
   Lavageeluting with ethylacetate/MeOH

Mode opératoire

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%).

Source