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. Author manuscript; available in PMC: 2016 Mar 1.
Published in final edited form as: Bioorg Med Chem. 2015 Jan 13;23(5):1027–1043. doi: 10.1016/j.bmc.2015.01.011

Scheme 5.

Scheme 5

Synthesis of phenoxyacetamide T3SS inhibitors with amide linker modifications.

Reagents and conditions: (a) amine, HATU, DIPEA, DMF, 20 °C; (b) alcohol, HATU, DIPEA, DMF, 20 °C; (c) 4-fluorophenylhydrazine or 4-flurorbenzylhydrazine, HATU, DIPEA, DMF, 20 °C; (d) O-benzylhydroxylamie, HATU, DIPEA, DMF, 20 °C; (e) N,O-dimethylhydroxylamine, HATU, DIPEA, DMF, 20 °C; (f) 4-fluorophenethylmagnesium bromide, THF, 0 °C.