Réaction #49178

Équation de réaction

2,2′-Dithio-bis(5-nitropyridine)

Succinate

4-Hydroxy-L-prolinol thiocholesterol succinate

triphenylphosphine

→

Thiocholesterol

Solvants

acetonitrile dichloroethane

dichloroethane

acetonitrile

Conditions de réaction

Traitement

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

Mode opératoire

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).

Source