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. 2014 Sep 30;57(21):8903–8927. doi: 10.1021/jm500989n

Scheme 3. Synthesis of 17a–g and 21.

Scheme 3

Reagents and conditions: (a) carboxylic acid, EDCI, HOBt, Et3N, DCM, 0 °C → rt, 15 h, 50–84%; (b) TFA, DCM, rt, 2 h, 77–100%; (c) 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea, HgCl2, Et3N, THF/MeOH, rt, 15 h, 16-31%; (d) NH3/MeOH, Raney Ni, 2.4 atm H2(g), 15 h, rt, 76%; (e) 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea, Et3N, DMF(ah), rt, 18 h, 87%; (f) TFA, DCM(ah), rt, 3 h, 77%; (g) 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea, Et3N, DMF(ah), rt, 2 days, 84%; (h) TFA, DCM(ah), rt, 3 h, 90%.