反応 #2275687

反応方程式

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

収率 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

収率 38.5%

溶媒

DMAC

DMAC

反応条件

後処理

1. 1
   workup.ADDITIONpoured over icewater (0.75 liter)
2. 2
   その他A white precipitate formed
3. 3
   その他This was collected
4. 4
   洗浄washed with cold water
5. 5
   workup.DISSOLUTIONThe filter cake was then dissolved in ethyl acetate
6. 6
   洗浄washed with brine
7. 7
   その他The organics were collected
8. 8
   乾燥dried over MgSO4
9. 9
   ろ過filtered
10. 10
    その他evaporated to dryness
11. 11
    その他The product was purified by silica column chromatography
12. 12
    洗浄eluting with Petroleum ether/ethyl acetate
13. 13
    洗浄Two peaks closely eluting at 80% ethyl acetate

実験手順

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%).

出典