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. Author manuscript; available in PMC: 2014 Feb 4.
Published in final edited form as: J Med Chem. 2008 Jul 22;51(15):4370–4373. doi: 10.1021/jm8002894

Scheme 2. Synthesis of Compounds 1 and 2a.

Scheme 2

a Reagents and conditions: (a) NaBH4, MeOH, rt, 30 min; (b) NaH (60%), DMF, 0 °C to rt, 1 h then methyl 5-bromovalerate, 0 to 70 °C, 12 h; (c) NH2OH·HCl, KOH, MeOH, rt, 15 min; (d) LiOH, THF, MeOH, H2O, 0 °C to rt, 1 h; (e) HCl·NH2(CH2)4COOMe, EDCI, HOBT, DIEA, DMF, 0 °C to rt, 12 h.