I'm now fairly confident that I've made TCMDC-123794 and TCMDC-123812. By fairly confident I mean that I've got a reasonable looking but crude 1H NMR and low res. mass spec of both of the compounds. They are not clean by NMR after a column and the yield of the reaction was pretty bad (~20%). Still this isn't too bad for a first go, using a quick and dirty acid chloride. Most of the mass seems to go toward turning the acid into the anhydride.
This page is intended as a place where people can discuss the student-led optimization of PZQ resolution. Relevant ELN is here, containing background here. Description of how students can help out is here (PDF). Paper will be assembled here.
PZQ can't be resolved as-is (unless anyone has any bright ideas how to resolve amides). One of the most promising strategies to prepare enantiopure praziquantel (using a strategy that starts from the racemate) is a classical resolution of praziquanamine (1, "PZQamine").
The synthesis of rac-PZQ via the Pictet-Spengler route was developed by the Korean Shin Poong Pharmaceutical Company and obtains very low production costs of US¢7 per 600 mg tablet of the drug.
Project A: Development of a low-cost enantioselective synthesis of PZQ. It's an open project, like everything on TSL. Meaning?: contributors can change anything they wish on these pages. If you wish to contribute: please don't leave comments here. Instead, edit the pages below directly or leave comments.
For an inexpensive route to rac-PZQ (and potentially the enantioenriched material), the relevant starting materials (below) are required. While prices may be obtained for these from commercial catalogues, we require realistic prices of these materials on a large (ton) scale to assess whether this approach to PZQ is economically viable. The starting materials are:
Last Wednesday I began some simple tests to try to find a good solvent for recrystallization, and here's some details and thoughts on what I've found so far.