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. Author manuscript; available in PMC: 2021 Oct 22.
Published in final edited form as: J Med Chem. 2020 Oct 15;63(20):11522–11547. doi: 10.1021/acs.jmedchem.0c00531

Scheme 3. Synthesis of Peptidomimetics 21a-c, 23a and 23ba.

Scheme 3.

aReagents and conditions: (a) Pd/C, H2, rt, overnight, 92%. (b) for 21a, 1-adamantanecarboxylic, HBTU, HOBt, DIPEA, CH2Cl2, rt, overnight, 67%; for 21b, Fmoc chloride, DIPEA, DMAP, DCM, rt, overnight, 73%; for 21c, acetyl chloride, DIPEA, DMAP, DCM, rt, overnight, 78%; (c) (i) LiOH, MeOH, rt, overnight; (ii) 1 N NaHSO4, 80%. (d) R4Br, NaHCO3, TBAI, DMF, rt, overnight, 71% for 23a; 69% for 23b.