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. Author manuscript; available in PMC: 2022 Apr 13.
Published in final edited form as: J Med Chem. 2020 Oct 29;63(21):12957–12977. doi: 10.1021/acs.jmedchem.0c01398

Scheme 3. Synthesis of Intermediate Iodide 32a.

Scheme 3.

aReagents and conditions: (i) sodium azide, ammonium chloride, methanol/water (91%); (ii) tert-butyl propiolate, N,N-diisopropylethylamine, acetic acid, dichloromethane (82% crude); (iii) diethylaminosulfur trifluoride, pyridine, dichloromethane (45%); (iv) 10% palladium hydroxide on carbon, hydrogen, ethyl acetate (101% crude); (v) 4-toluenesulfonyl chloride, 4-dimethylaminopyridine, dichloromethane (84% crude); sodium iodide, acetone (91%).