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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 1. Synthesis of Cyclic and Acyclic Amino Acid Derivatives 16a–xa.

Scheme 1.

a(a) (i) 9-BBN, THF, 66 °C, 1 h; (ii) 4-iodobenzonitrile, Pd(dppf)Cl2·CH2Cl2, KOH(aq), THF, 66 °C, 4 h, 96%; (b) NH2OH·HCl, EtOH, 78 °C, 2 h, 92%; (c) N-Boc-amino acid or N,N-dimethylglycine, DIEA, HCTU, DMF, 100 °C, 6 h, 46–76%; (d) 4 M HCl/dioxane, DCM, rt, 2 h, 33–89%; (e) Ac2O, TEA, neat, rt, 0.5 h, 82%.