Reacción #363296

Ecuación de reacción

2-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine t-butyl ester

anisole

carbon tetrachloride

→

title compound

Rendimiento 58.2%

2-mercapto-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine

Rendimiento 58.2%

Disolventes

dichloromethane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaCool in an ice bath
2. 2
   Otrodegas
3. 3
   workup.ADDITIONAdd trifluoroacetic acid (4 mL)
4. 4
   workup.WAITAfter 3 hours
5. 5
   Otropurge with hydrogen sulfide (gas) for about 10 minutes
6. 6
   FiltraciónFilter
7. 7
   Otroevaporate in vacuo
8. 8
   Otroto give a residue
9. 9
   Otroevaporate in vacuo
10. 10
    Otroto give a residue
11. 11
    OtroTriturate the residue with hexane

Procedimiento

Combine 2-(4-methoxybenzylthio)-pentanoyl-(L)-homophenylalanyl-(L)-phenylalanine t-butyl ester (0.20 g, 0.33 mmol), mercury (II) acetate (0.134 g, 0.42 mmol), and anisole (0.37 mL, 3.4 mmol) in dichloromethane (9 mL). Cool in an ice bath and degas by repeatedly applying vacuum and filling the vessel with nitrogen, Add trifluoroacetic acid (4 mL). After 1 hour, warm to ambient temperature. After 3 hours, purge with hydrogen sulfide (gas) for about 10 minutes. Filter and evaporate in vacuo to give a residue. Repeatedly, combine the residue and carbon tetrachloride and evaporate in vacuo to give a residue. Triturate the residue with hexane to give the title compound as a solid (85 mg, 57%).

Fuente