반응 #2275687

반응 방정식

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

수율 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

수율 38.5%

용매

DMAC

DMAC

반응 조건

후처리

1. 1
   workup.ADDITIONpoured over icewater (0.75 liter)
2. 2
   기타A white precipitate formed
3. 3
   기타This was collected
4. 4
   세척washed with cold water
5. 5
   workup.DISSOLUTIONThe filter cake was then dissolved in ethyl acetate
6. 6
   세척washed with brine
7. 7
   기타The organics were collected
8. 8
   건조dried over MgSO4
9. 9
   여과filtered
10. 10
    기타evaporated to dryness
11. 11
    기타The product was purified by silica column chromatography
12. 12
    세척eluting with Petroleum ether/ethyl acetate
13. 13
    세척Two peaks closely eluting at 80% ethyl acetate

실험 절차

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%).

출처