Reacción #49178

Ecuación de reacción

2,2′-Dithio-bis(5-nitropyridine)

Succinate

4-Hydroxy-L-prolinol thiocholesterol succinate

triphenylphosphine

→

Thiocholesterol

Disolventes

acetonitrile dichloroethane

dichloroethane

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrowrist-action shaker (5 mins)
2. 2
   workup.STIRRINGThe suspension was agitated for 4 h
3. 3
   FiltraciónThe CPG was filtered through a sintered funnel
4. 4
   Lavadowashed with acetonitrile, dichloromethane and ether successively

Procedimiento

Succinate 27 (2.1 g, 1.9 mmol) was dissolved in dichloroethane (8 mL). To that solution DMAP (0.228 g, 1.9 mmol) was added. 2,2′-Dithio-bis(5-nitropyridine) (0.58 g, 1.9 mmol) in acetonitrile/dichloroethane (3:1, 8 mL) was added successively. To the resulting solution triphenylphosphine (0.49 g, 1.9 mmol) in acetonitrile (4 ml) was added. The reaction mixture turned bright orange in color. The solution was agitated briefly using wrist-action shaker (5 mins). Long chain alkyl amine-CPG (LCAA-CPG) (12 g, 1860 μmoles, 155 μm/g) was added. The suspension was agitated for 4 h. The CPG was filtered through a sintered funnel and washed with acetonitrile, dichloromethane and ether successively. Unreacted amino groups were masked using acetic anhydride/pyridine. The loading capacity of the CPG 28 was measured by taking UV measurement. (57 μM/g).

Fuente