Reacción #2146720

Ecuación de reacción

NaOH

H-Glu-Glu Adamantane

β-Cyclodextrin DTBP

Z-Glu(Bn)-OSu

H-Glu(Bn)-OH

sodium bicarbonate

→

solid 6

β-Cyclodextrin

Disolventes

THF

THF

CH3CN

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroTHF and CH3CN was evaporated under high vacuum
2. 2
   workup.ADDITIONTo the aqueous mixture was added 1 N HCl
3. 3
   OtroPrecipitation
4. 4
   ExtracciónThe mixture was extracted with chloroform (3×30 mL)
5. 5
   SecadoThe organic phase was dried with MgSO4
6. 6
   OtroMgSO4 was removed by filtration
7. 7
   OtroOrganic solvent was evaporated

Procedimiento

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.

Fuente