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13th April 2011 @ 07:20
Synthesis of [i]rac[/i]-PZQamine by an acidic hydrolysis of [i]rac[/i]-PZQ [data=size:500x160]639[/data] See also: [*] [url=http://www.ourexperiment.org/racres_pzq/1521]Hydrolysis of rac-PZQ (MW2-14)[/url] [*] [url=http://www.ourexperiment.org/racres_pzq/1175]Hydrolysis of rac-PZQ (MW2-13)[/url] [*] [url=http://www.thesynapticleap.org/node/296]Optimizing the acid cleavage conditions II[/url] [b]Hazard and Risk Assessment:[/b] [data=text]641[/data] Start time: 5:00 PM 13/04/2011 End time: 10:00 AM 14/04/2011 [b]Procedure:[/b] [url=http://www.ourexperiment.org/racres_pzq/1700]rac-PZQ[/url] (20.0 g, 64.0 mmol, M.W. 312.4 g/mol) was dissolved in a mixture of EtOH (150 mL) and 1N HCl (600 mL, 53.0 mL of 11.3 N HCl solution (35%) in 547 mL water) and heated to reflux for 17 h. Reaction monitored by TLC showed a complete consumption of PZQ (TLC, ethyl acetate, Rf ~0.5 for PZQ). Work-up: Solution was cooled to room temperature, washed with EtOAc (4 times 15 mL), basified with NaOH solution (5 N) to ph 12, extracted with DCM (5 x 30 mL), washed with brine, dried over NaSO4, evaporated under reduced pressure. - the pale yellow oil became a solid after 1 h under high vac Yield: 11.0 g (54.5 mmol, 85%) colourless solid (turning pale red/orange after a few hours at r.t.) [M.W. = 202.1 g/mol]