تفاعل #2275687

معادلة التفاعل

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

المردود 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

المردود 38.5%

المذيبات

DMAC

DMAC

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONpoured over icewater (0.75 liter)
2. 2
   أخرىA white precipitate formed
3. 3
   أخرىThis was collected
4. 4
   غسيلwashed with cold water
5. 5
   workup.DISSOLUTIONThe filter cake was then dissolved in ethyl acetate
6. 6
   غسيلwashed with brine
7. 7
   أخرىThe organics were collected
8. 8
   تجفيفdried over MgSO4
9. 9
   ترشيحfiltered
10. 10
    أخرىevaporated to dryness
11. 11
    أخرىThe product was purified by silica column chromatography
12. 12
    غسيلeluting with Petroleum ether/ethyl acetate
13. 13
    غسيلTwo peaks closely eluting at 80% ethyl acetate

الإجراء التجريبي

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%).

المصدر