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. Author manuscript; available in PMC: 2023 Feb 9.
Published in final edited form as: J Med Chem. 2022 May 24;65(11):7656–7681. doi: 10.1021/acs.jmedchem.1c02171

Scheme 6. Synthesis of 1,3,4-Oxadiazole 47a.

Scheme 6.

a(a) Hydrazine hydrate, EtOH, 80 °C, 20 h, 67%; (b) (i) N-Boc-GABA, DIEA, HCTU, MeCN, rt, 18 h; (ii) DIEA, TsCl, MeCN, rt, 18 h, 79%; (c) (i) 1-decene, 9-BBN, THF, 66 °C, 1 h; (ii) aryl iodide, Pd(dppf)Cl2·CH2Cl2, KOH(aq), THF, 66 °C, 4 h, 79%; (d) 4 M HCl/dioxane, DCM, rt, 2 h, 76%.