反応 #1244258

反応方程式

NaOH

H-Glu-Glu Adamantane

β-cyclodextrin DTBP

Z-Glu(Bn)-OSu

H-Glu(Bn)-OH

sodium bicarbonate

→

solid 6

β-cyclodextrin

溶媒

THF

THF

CH3CN

water

反応条件

後処理

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

実験手順

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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