Реакция #363296

Уравнение реакции

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

anisole

carbon tetrachloride

→

title compound

Выход 58.2%

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

Выход 58.2%

Растворители

dichloromethane

Условия реакции

Обработка

1. 1
   ТемператураCool in an ice bath
2. 2
   Другоеdegas
3. 3
   workup.ADDITIONAdd trifluoroacetic acid (4 mL)
4. 4
   workup.WAITAfter 3 hours
5. 5
   Другоеpurge with hydrogen sulfide (gas) for about 10 minutes
6. 6
   ФильтрацияFilter
7. 7
   Другоеevaporate in vacuo
8. 8
   Другоеto give a residue
9. 9
   Другоеevaporate in vacuo
10. 10
    Другоеto give a residue
11. 11
    ДругоеTriturate the residue with hexane

Методика

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%).

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