Réaction #1244258

Équation de réaction

NaOH

H-Glu-Glu Adamantane

β-cyclodextrin DTBP

Z-Glu(Bn)-OSu

H-Glu(Bn)-OH

sodium bicarbonate

→

solid 6

β-cyclodextrin

Solvants

THF

THF

CH3CN

water

Conditions de réaction

Traitement

1. 1
   AutreTHF and CH3CN was evaporated under high vacuum
2. 2
   workup.ADDITIONTo the aqueous mixture was added 1 N HCl
3. 3
   AutrePrecipitation
4. 4
   ExtractionThe mixture was extracted with chloroform
5. 5
   SéchageThe organic phase was dried with MgSO4
6. 6
   AutreMgSO4 was removed by filtration
7. 7
   AutreOrganic solvent was evaporated

Mode opératoire

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.

Source