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. 2014 Apr 28;57(10):4173–4184. doi: 10.1021/jm5000672

Scheme 4. Synthesis of Aqueous Soluble Hydroxyethyl Ether Cinnamic Amide Derivatives.

Scheme 4

Reagents and conditions: (a) 2-tert-butyldimethylsilyloxyethanol, PPh3, DIAD,THF, reflux, 36 h, 70%; (b) 1 N NaOH, THF, 2 N HCl, 801%; (c) 3a, 3b, or 3k, EDCl, DMAP, DCM/DMF (5:1), 80%.