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Synthesis of WRR-483 (2):

By Yen Ting Chen (361838), Linda S. Brinen (247688), Iain D. Kerr (247678), Elizabeth Hansell (203763), Patricia S. Doyle (345076), James H. McKerrow (113918) and William R. Roush (361839)


<p>(a) (i) benzyl alcohol (BnOH), 4-dimethylaminopyridine, 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDC), <i>N-</i>methylmorpholine, CH<sub>2</sub>Cl<sub>2</sub>; (ii) piperidine, CH<sub>2</sub>Cl<sub>2</sub>, 90% (two steps); (b) (i) triphosgene, sodium bicarbonate (NaHCO<sub>3</sub>), CH<sub>2</sub>Cl<sub>2</sub>; (ii) <i>N</i>-methylpiperazine, CH<sub>2</sub>Cl<sub>2</sub>, 93% (two steps); (c) H<sub>2</sub>, 5% palladium on carbon (Pd/C), MeOH, 92% (d) (i) trifluoroacetic acid (TFA), CH<sub>2</sub>Cl<sub>2</sub>; (ii) <b>6</b>, N-hydroxybenzotriazole (HOBT), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDC), <i>N</i>-methylmorpholine, dimethyl formamide (DMF), CH<sub>2</sub>Cl<sub>2</sub>, 84%; (g) 3:1 TFA:CH<sub>2</sub>Cl<sub>2</sub>, 86%.</p

Topics: Biochemistry, Physics, Medicine, Pharmacology, Chemistry, wrr-483
Year: 2013
DOI identifier: 10.1371/journal.pntd.0000825.g002
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Provided by: FigShare
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