Reacción #969873

Ecuación de reacción

Z-Val-Pro-Val-Pro-OH

1-hydroxibenzotriazol

N,N′-diisopropylcarbodiimide

Ara-C

→

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

Rendimiento 22.0%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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)

Fuente