Reaktion #363296

Reaktionsgleichung

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

anisole

carbon tetrachloride

→

title compound

Ausbeute 58.2%

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

Ausbeute 58.2%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturCool in an ice bath
2. 2
   Sonstigedegas
3. 3
   workup.ADDITIONAdd trifluoroacetic acid (4 mL)
4. 4
   workup.WAITAfter 3 hours
5. 5
   Sonstigepurge with hydrogen sulfide (gas) for about 10 minutes
6. 6
   FiltrationFilter
7. 7
   Sonstigeevaporate in vacuo
8. 8
   Sonstigeto give a residue
9. 9
   Sonstigeevaporate in vacuo
10. 10
    Sonstigeto give a residue
11. 11
    SonstigeTriturate the residue with hexane

Vorschrift

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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