Réaction #2275687

Équation de réaction

triethylamine

acetic acid 2-acetoxy-1-(3,5-bis-chlorocarbonyl-2,4,6-triiodo-phenylcarbamoyl)-ethyl ester

2-[(2,2-Dimethyl-[1,3]dioxolan-4-yl-methyl)-amino]-ethanol

→

desired product

Rendement 38.5%

Acetic acid 2-acetoxy-1-{3-chlorocarbonyl-5-[(2,2-dimethyl-[1,3]-dioxolan-4-ylmethyl)-(2-hydroxy-ethyl)-carbamoyl]-2,4,6-triiodo-phenylcarbamoyl}-ethyl ester

Rendement 38.5%

Solvants

DMAC

DMAC

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONpoured over icewater (0.75 liter)
2. 2
   AutreA white precipitate formed
3. 3
   AutreThis was collected
4. 4
   Lavagewashed with cold water
5. 5
   workup.DISSOLUTIONThe filter cake was then dissolved in ethyl acetate
6. 6
   Lavagewashed with brine
7. 7
   AutreThe organics were collected
8. 8
   Séchagedried over MgSO4
9. 9
   Filtrationfiltered
10. 10
    Autreevaporated to dryness
11. 11
    AutreThe product was purified by silica column chromatography
12. 12
    Lavageeluting with Petroleum ether/ethyl acetate
13. 13
    LavageTwo peaks closely eluting at 80% ethyl acetate

Mode opératoire

To a ice cooled solution of acetic acid 2-acetoxy-1-(3,5-bis-chlorocarbonyl-2,4,6-triiodo-phenylcarbamoyl)-ethyl ester (20 g, 0.026 mol) in anhydrous DMAC (20 ml) were added dropwise a solution of 2-[(2,2-Dimethyl-[1,3]dioxolan-4-yl-methyl)-amino]-ethanol (4.6 g, 0.026 mol) in DMAC (20 mL) followed by triethylamine (˜3 g). The mixture was stirred at room temperature for 24 h and then poured over icewater (0.75 liter). A white precipitate formed. This was collected and washed with cold water. The filter cake was then dissolved in ethyl acetate and washed with brine. The organics were collected, dried over MgSO4, filtered and evaporated to dryness. The product was purified by silica column chromatography eluting with Petroleum ether/ethyl acetate. Two peaks closely eluting at 80% ethyl acetate were analysed by NMR and mass spec, and show to both contain the desired material. These were combined post analysis to give the desired product (10 mmol, Yield=38%).

Source