Triflic Acid Catalysed PS Reactions
Community
schisto research communityThe use of catalytic triflic acid TfOH in the Pictet-Spengler reaction was initially performed as a control for the silver(I) triflate (AgOTf) catalysed reaction (here). All early experiments using TfOH were performed with the dimethoxy N-benzoyl PZQ analogue and catalyst loading was reduced down to 5% (KAB8-7 & KAB8-8, KAB8-9). Interestingly, the yield increased as the acid loading was reduced.
The conditions were mostly optimised before the experiment was run with PZQ and the 3 analogues at 10 and 5% catalyst loadings. The non-dimethoxy peptide acetals (PZQ and the N-benzoyl PZQ analogue) did not go to completion.*
I'm still in the process of recrystallising and/or attempting to purify the products so the experiments and summary are incomplete (as of 28/02/12).
10 mol% TfOH catalysed PS reactions
- The dimethoxy N-benzoyl PZQ analogue (KAB8-12).
- The dimethoxy PZQ analogue (KAB1-4).
- The N-benzoyl PZQ analogue (KAB7-3).
- PZQ (KAB3-17).
5 mol% TfOH catalysed PS reactions
- The dimethoxy analogues (KAB8-14 and KAB1-5).
- The N-benzoyl analogue and PZQ (KAB17-1 and KAB13-2).
Yield Summary
I'm still attempting to re-crystallise the praziquantel enamide and the dimethoxy PZQ analogue. The table below will be updated as soon as those procedures are complete.
