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4th June 2010 @ 08:12
Looking for the right acid strength and optimizing reaction conditions for the Pictet-Spengler cyclisation of MW29-4 to rac-PZQ (MW31)

Reaction Scheme


Table1


Hazard and Risk Assessment:
Reaction Class: 2
Hazards: X Irritant, C Corrosive, F Flammable
Risk rating: U = Unlikely

Start time (Trial 1-3): 4:00 pm
End time:

MW31-1:
MW29-4 (50.0 mg, 145 µmol) was dissolved in toluene (2 mL), phenylphosphinic acid (20.6 mg, 145 µmol, 1, eq.) was added and stirred at rt.

MW31-2:
MW29-4 (50.0 mg, 145 µmol) was dissolved in toluene (2 mL), p-TsOH (24.9 mg, 145µmol, 1 eq.) was added and stirred at rt.


MW31-2:
MW29-4 (50.0 mg, 145 µmol) was dissolved in trifluoroacetic acid (1 mL) and stirred at rt.
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Reaction Scheme
Table1