تفاعل #363296

معادلة التفاعل

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

anisole

carbon tetrachloride

→

title compound

المردود 58.2%

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

المردود 58.2%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةCool in an ice bath
2. 2
   أخرىdegas
3. 3
   workup.ADDITIONAdd trifluoroacetic acid (4 mL)
4. 4
   workup.WAITAfter 3 hours
5. 5
   أخرىpurge with hydrogen sulfide (gas) for about 10 minutes
6. 6
   ترشيحFilter
7. 7
   أخرىevaporate in vacuo
8. 8
   أخرىto give a residue
9. 9
   أخرىevaporate in vacuo
10. 10
    أخرىto give a residue
11. 11
    أخرىTriturate the residue with hexane

الإجراء التجريبي

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%).

المصدر