Réaction #969873

Équation de réaction

Z-Val-Pro-Val-Pro-OH

1-hydroxibenzotriazol

N,N′-diisopropylcarbodiimide

Ara-C

→

Z-Val-Pro-Val-Pro Ara-C

Rendement 22.0%

Solvants

dimethylformamide

Conditions de réaction

Traitement

1. 1
   Autrewas continued until complete disappearance of the starting material (overnight)
2. 2
   AutreThen, the solvent was evaporated
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate
4. 4
   Lavagewashed with citric acid (10%), NaHCO3 (10%) and brine
5. 5
   SéchageThe organic layer was dried (Na2SO4)
6. 6
   Autreevaporated to dryness
7. 7
   Autreleaving a residue that
8. 8
   Autrewas purified by CCTLC on the chromatotron with dichloromethane:methanol (20:1)
9. 9
   Autreto give D (22% yield)

Mode opératoire

A solution of Z-Val-Pro-Val-Pro-OH [SEQ ID NO:9] (134.4 mg, 0.24 mmol) in dimethylformamide (1.5 mL), was successively treated at room temperature with 1-hydroxibenzotriazol (33.3 mg, 0.24 mmol), N,N′-diisopropylcarbodiimide (38.4 μL, 0.24 mmol) and Ara-C (50 mg, 0.20 mmol). The stirring was continued until complete disappearance of the starting material (overnight). Then, the solvent was evaporated, and the residue was dissolved in ethyl acetate and washed with citric acid (10%), NaHCO3 (10%) and brine. The organic layer was dried (Na2SO4) and evaporated to dryness leaving a residue that was purified by CCTLC on the chromatotron with dichloromethane:methanol (20:1) to give D (22% yield)

Source