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Synthesis of WRR-483 (2):

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posted on 2013-02-20, 23:32 authored by Yen Ting Chen, Linda S. Brinen, Iain D. Kerr, Elizabeth Hansell, Patricia S. Doyle, James H. McKerrow, William R. Roush

(a) (i) benzyl alcohol (BnOH), 4-dimethylaminopyridine, 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDC), N-methylmorpholine, CH2Cl2; (ii) piperidine, CH2Cl2, 90% (two steps); (b) (i) triphosgene, sodium bicarbonate (NaHCO3), CH2Cl2; (ii) N-methylpiperazine, CH2Cl2, 93% (two steps); (c) H2, 5% palladium on carbon (Pd/C), MeOH, 92% (d) (i) trifluoroacetic acid (TFA), CH2Cl2; (ii) 6, N-hydroxybenzotriazole (HOBT), 1-ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride (EDC), N-methylmorpholine, dimethyl formamide (DMF), CH2Cl2, 84%; (g) 3:1 TFA:CH2Cl2, 86%.

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