反应 #1244258

反应方程式

NaOH

H-Glu-Glu Adamantane

β-cyclodextrin DTBP

Z-Glu(Bn)-OSu

H-Glu(Bn)-OH

sodium bicarbonate

→

solid 6

β-cyclodextrin

溶剂

THF

THF

CH3CN

water

反应条件

后处理

1. 1
   其他THF and CH3CN was evaporated under high vacuum
2. 2
   workup.ADDITIONTo the aqueous mixture was added 1 N HCl
3. 3
   其他Precipitation
4. 4
   萃取The mixture was extracted with chloroform
5. 5
   干燥The organic phase was dried with MgSO4
6. 6
   其他MgSO4 was removed by filtration
7. 7
   其他Organic solvent was evaporated

实验过程

Compound numbers below refer to the above scheme. I. Synthesis of H-Glu-Glu-Adamantane 7. H-Glu(Bn)-OH (3.55 g, 15 mmol) was dissolved in water (16 mL) containing sodium bicarbonate (1.26 g, 15 mmol). To the mixture was added Z-Glu(Bn)-OSu (4.68 g, 10 mmol) in THF (30 mL). To the mixture was added another 30 mL THF, 20 mL CH3CN and then 2N NaOH 10 mL. The solution was stirred for 16 hours at room temperature. THF and CH3CN was evaporated under high vacuum. To the aqueous mixture was added 1 N HCl to adjust the pH to 3. Precipitation was observed. The mixture was extracted with chloroform. (3×30 mL). The organic phase was dried with MgSO4. MgSO4 was removed by filtration. Organic solvent was evaporated to give white sticky solid 6. 6 was used for next step reaction without further purification.

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