Реакция #2275687

Уравнение реакции

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

Выход 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

Выход 38.5%

Растворители

DMAC

DMAC

Условия реакции

Обработка

1. 1
   workup.ADDITIONpoured over icewater (0.75 liter)
2. 2
   ДругоеA white precipitate formed
3. 3
   ДругоеThis was collected
4. 4
   Промывкаwashed with cold water
5. 5
   workup.DISSOLUTIONThe filter cake was then dissolved in ethyl acetate
6. 6
   Промывкаwashed with brine
7. 7
   ДругоеThe organics were collected
8. 8
   Сушкаdried over MgSO4
9. 9
   Фильтрацияfiltered
10. 10
    Другоеevaporated to dryness
11. 11
    ДругоеThe product was purified by silica column chromatography
12. 12
    Промывкаeluting with Petroleum ether/ethyl acetate
13. 13
    ПромывкаTwo peaks closely eluting at 80% ethyl acetate

Методика

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%).

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