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23rd November 2011 @ 23:22
**I've been locked out of the previous post due to mix up in google accounts**

Acid-mediated Pictet-Spengler of MW51 to give N-benzoyl-derivative of PZQ MNR14-1 - comparing the rates of reaction versus the activated examples MNR11, MNR12 and MNR13-1

MNR14-1%20scheme.png

MNR14-1%20table.PNG

Hazard and Risk Assessment:
As for MNR12-2

Procedure
MW51 (95 mg, 0.28 mmol) was stirred with methanesulfonic acid (1.82 mL, 28 mmol) at room temperature and after 1 hour (first TLC) all the starting material had been consumed. The reaction was quenched with saturated sodium carbonate and extracted with EtOAc (20 mL x2). The organic fractions were dried over magnesium sulfate, filtered and concentrated under reduced pressure.

Crude - 60 mg as a yellow oil that showed signs of slowly crystallizing after 24 hours

1H MNR14-1 Crude
1H MNR14-1 vs MNR12-1
Linked Entries
Attached Files
mnr14-1_crude.pdf
mnr14-1.pdf