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. Author manuscript; available in PMC: 2023 Sep 16.
Published in final edited form as: J Med Chem. 2021 Jul 21;64(15):11267–11287. doi: 10.1021/acs.jmedchem.1c00628

Scheme 3. Synthesis of 13C-labeled 12a.

Scheme 3.

a(i) 1-methylimidazole, MsCl, DCM, 45 °C, (ii) [1-13C] glycine, Ni(NO3)2·6H2O, KOH, MeOH, 60 °C, (iii) (2-(benzyloxy)phenyl)methanol, cyanomethylenetributylphosphorane (CMBP), toluene, 120 °C, (iv) 8-quinolinol, MeCN/H2O, 40 °C, (v) Et3N, Boc anhydride, dioxane/H2O, (vi) N,O-dimethylhydroxylamine, DIPEA, T3P, DCM, (vii) TFA, DCM; NMePip-Phe-OH, DIPEA, T3P, DCM, (viii) LAH, THF, 0 °C, and (ix) Pd/C, H2, MeOH.