反应 #5242

反应方程式

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

[(amino)carbonyl]amino-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid

→

oxanosine

溶剂

water

CH3OH

反应条件

后处理

1. 1
   其他The reaction was quenched by addition of excess 60% aqueous acetic acid
2. 2
   workup.WAITAfter 30 minutes
3. 3
   workup.ADDITIONthe mixture was diluted with water
4. 4
   浓缩concentrated
5. 5
   其他to remove CH3OH
6. 6
   其他The resulting powder (100 mg) was chromatographed on reverse phase silica gel [
7. 7
   洗涤10 g, flash, stepwise gradient elution
8. 8
   workup.ADDITIONFractions containing the product
9. 9
   浓缩concentrated under reduced pressure

实验过程

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (78 mg, 0.41 mmol) was added to a solution of 5-[[(amino)carbonyl]amino-1-(β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid (19 mg, 0.063 mmol) in water (2 mL) and CH3OH (5 mL) and the mixture was stirred at room temperature overnight. The reaction was quenched by addition of excess 60% aqueous acetic acid. After 30 minutes, the mixture was diluted with water, concentrated to remove CH3OH and lyophilized. The resulting powder (100 mg) was chromatographed on reverse phase silica gel [10 g, flash, stepwise gradient elution: water (200 mL), 10% CH3OH in water (v/v, 100 mL), 20% CH3OH in water (v/v, 100 mL), 10-mL fractions]. Fractions containing the product were combined, concentrated under reduced pressure and lyophilized to give oxanosine: 16 mg (89%).

来源