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. Author manuscript; available in PMC: 2020 Feb 9.
Published in final edited form as: J Med Chem. 2019 Apr 9;62(8):4193–4203. doi: 10.1021/acs.jmedchem.9b00378

Scheme 1: General Synthetic Scheme for C-6/N-1 Substituted Peptidomimetics.

Scheme 1:

a Reagents and conditions: (A) Boc anhydride, DMAP, DIPEA, DCM, reflux or (B) Acetic anhydride, cyclopropanecarbonyl chloride, or benzoyl chloride, DIPEA, DCM. (C) NBS, benzoyl peroxide, CCl4, reflux. (D) R2-boronic acid pinacol ester, Pd(dppf)Cl2, K2CO3, 3:1 acetone/water, 80°C, or (E) tetrahydroisoquinoline-HCl, K2CO3, DMF, r.t. (F) (R)-(+)-2-methyl-2-propanesulfinamide, Ti(OEt)4, THF, 0°C to reflux, then NaBH4, THF, −78°C to r.t. (G) HCl, 1,4-dioxane, r.t., then di-Boc 2,6-dimethyl-L-tyrosine, PyBOP, DIPEA, DMF, r.t., then TFA, DCM, r.t.