Reacción #531796

Ecuación de reacción

compound 25

N-(11-(p-tolyloxy)undecyl)-3-(tritylthio)propaneamide

trifluoroacetic acid

triethylsilane

→

N-(11-(p-tolyloxy)undecyl)-3-mercaptopropaneamide

Disolventes

methylene chloride

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Otroto obtain a brown-colored solution
2. 2
   workup.DISTILLATIONthe supernatant solution was distilled away under reduced pressure
3. 3
   OtroThe solid obtained
4. 4
   Lavadowas washed twice with 30 ml of aqueous saturated sodium hydrogen carbonate solution and twice with 30 ml of saturated brine
5. 5
   Otrothe desiccant agent was removed by filtration
6. 6
   workup.DISTILLATIONthe solvent of the filtrate was distilled away under reduced pressure
7. 7
   OtroThe reaction mixture was purified by chromatography, and 0.1 g of the compound f, which
8. 8
   Otrowas obtained

Procedimiento

The compound 25 (0.181 g) was dissolved in 1 ml of methylene chloride, and 0.5 ml of trifluoroacetic acid was added to that while being stirred, to obtain a brown-colored solution. After a white-colored precipitate was generated by adding 0.16 ml of triethylsilane, the supernatant solution was distilled away under reduced pressure. The solid obtained was dissolved by the new addition of 20 ml of methylene chloride, and was washed twice with 30 ml of aqueous saturated sodium hydrogen carbonate solution and twice with 30 ml of saturated brine. After the collected organic phase was dehydrated with magnesium sulfate, the desiccant agent was removed by filtration, and the solvent of the filtrate was distilled away under reduced pressure. The reaction mixture was purified by chromatography, and 0.1 g of the compound f, which was a white solid, was obtained.

Fuente