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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 2.

Scheme 2

Synthesis of phenoxyacetamide T3SS inhibitors with varying substituents on the phenoxide ring.

Reagents and conditions: (a) ethyl-2-bromopropionate, K2CO3, DMF, 50 °C; (b) KOH, MeOH/H2O, 20 °C; (c) piperonylamine, HATU, DIPEA, DMF, 20 °C; (d) Na metal, ethyl lactate, diglyme, 200 °C.