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. Author manuscript; available in PMC: 2018 Jun 15.
Published in final edited form as: Bioorg Med Chem. 2017 Nov 10;25(24):6707–6717. doi: 10.1016/j.bmc.2017.11.015

Scheme 2.

Scheme 2

Synthetic path for prodrug 11. Reagents and conditions: (i) EEDQ, DCM-DMF, 87%; (ii) 25% Piperidine/DMF, 65% (iii) Fmoc-Ala-OH, EEDQ, DCM-DMF, RT, 80%; (iv) DMAP, DSC, DCM, Emetine·2HCl, DIEA, Argon; (v) 25% Piperidine/DMF, 50%; (vi) HATU, 4, DIEA, DMF. (vii) 2% Hydrazine in DMF, 40%.