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. Author manuscript; available in PMC: 2017 Dec 22.
Published in final edited form as: J Med Chem. 2016 Dec 2;59(24):11148–11160. doi: 10.1021/acs.jmedchem.6b01450

Scheme 3.

Scheme 3

Synthetic route to 1114a

a Reagents and conditions: (a) 50% aq. H3PO2, conc. H2SO4, Cu2O, 1M aq. NaNO2, MeOH, 0 °C to rt, 2 h 30 min, 22%; (b) triphosgene, THF, rt, 1 h, 98%; (c) chloromethylsulfonyl chloride, Et3N, DCM, 0 °C to rt, 12 h then 2N NaOH, rt, 2 h 30 min, 60%-72%; (d) 25, NaOEt, DMF, 130 °C, 1 h, 33%-72%.