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Racemization of PZQ and PZQamine
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22nd March 2011 @ 06:53
Continuation of the racemization experiments on (R)-(-)-PZQ (MW48-5)

Scheme MW55.png


See also:
Experiments on the racemization of (R)-PZQ (MW55-1 to MW55-3)
Racemization of S-(+)-PZQamine with Raney Nickel (MW50-6, MW50-7)

Hazard and Risk Assessment:
HRAF MW50.pdf


Start time: 6:00 PM 22/03/2011
End time: 9:00 PM 25/03/2011

MW55-4 (1 atm hydrogen)
To a solution of (R)-(-)-PZQ (20.7 mg, 66.3 µmol, MW: 312.4 g/mol) in ethanol (2 mL) was added Raney nickel (778 µg, 133 µmol, 0.2 eq.; 7.8 µL suspension of Raney nickel (Suspension in water ~0.1 g/mL), M.W. (Ni) 58.7 g/mol) under a atmosphere of hydrogen and heated to 70°C for 2.5 d.
Chiral HPLC (Chiralcel OD-H, hexane/iso-propanol/Et3N = 60/40/0.1, 0.7 ml/min flow rate):
- no racemization of (R)-PZQ (RT: (R)-PZQ: 11.2/11.6 min, (S)-PZQ: 13.3 min)
HPLC MW55-4.jpg
HPLC MW55-4 + rac-PZQ.jpg


MW55-7 (1000 kPa hydrogen) -> moved to Racemization of (R)-PZQ with Raney Nickel under high pressure and high temperature (MW55-7)
Attached Files
HPLC MW55-4.jpg
HPLC MW55-4 + rac-PZQ.jpg