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. 2022 Sep 30;65(19):13328–13342. doi: 10.1021/acs.jmedchem.2c01131

Scheme 1. Synthesis and structures of 11–13.

Scheme 1

Reagents and conditions: (a) H2SO4, NaNO2, H2O, 0–5 °C; (b) SOCl2, MeOH, 0 °C; (c) Tf2O, 2,6-lutidine, DCM, 0 °C; (d) tert-butyl (2-oxo-1,2-dihydropyridin-3-yl)carbamate, NaH, THF, 0 °C; (e) LiOH.H2O, MeOH, H2O, RT; (f) methyl (S)-2-amino-3-((S)-2-oxopyrrolidin-3-yl)propanoate hydrochloride, EDC·HCl, HOBt, TEA, DCM, 0 °C; (g) NaBH4, MeOH, RT; (h) DMP, NaHCO3, DCM, RT; (i) benzyl isocyanide, AcOH, DCM, RT; (j) LiOH.H2O, MeOH, H2O, RT; (k) DMP, NaHCO3, DCM, RT.