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20th February 2012 @ 22:12
PS = Pictet-Spengler

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Summary and Conclusion
No reaction of the dimethoxy N-benzoyl PZQ analogue peptide acetal in the presence of silver chloride.
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START: 21/02/12
FINISH: 21/02/12

Background




Hazard and Risk Assessment
Hazard and Risk Assessment KAB8-13


Previous Related Experiments
The TfOH catalysed PS* reaction to give the dimethoxy N-benzoyl PZQ analogue (KAB8-12)

Following Experiments
TfOH catalysed PS* reactions to give the dimethoxy PZQ analogues (KAB8-14 & KAB1-5)

Procedure
MNR10-2 (253.6 mg, 0.553 mmol) was dissolved in toluene (25 mL) before the addition of AgCl (29.1 mg, 0.203, 37 mol%) at rt. The mixture was immediately placed in a pre-heated oil bath at 90 °C and reflux heated from 10:55.

Taken off heat after 1 hour.

Monitoring the Reaction Progress by TLC
All TLCs were eluted with EtOAc/hexane, 5:3, v/v and stained with KMnO4.
TLC of reaction mixture (5 min)
TLC of reaction mixture (15 min)
TLC of reaction mixture (30 min)
TLC of reaction mixture (1 h)


Summary and Conclusion
No reaction of the dimethoxy N-benzoyl PZQ analogue peptide acetal in the presence of silver chloride.

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NOTES 21/02/12
- Suspect the silver has been reduced - Black solid in flask.
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Linked Posts
Attached Files
Hazard and Risk Assessment KAB8-13
Scheme KAB8-13
Table KAB8-13
TLC of reaction mixture (5 min)
Reaction mixture (5 min)
TLC of reaction mixture (15 min)
TLC of reaction mixture (30 min)
TLC of reaction mixture (1 h)