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. Author manuscript; available in PMC: 2023 Feb 10.
Published in final edited form as: J Med Chem. 2022 Jan 26;65(3):2409–2433. doi: 10.1021/acs.jmedchem.1c01852

Scheme 2. Synthetic Strategies for Extension at the 4-Carboxyl Group on a 4-Benzyloxyimino Substituenta.

Scheme 2.

a Reagents and conditions: (i) 1 N NaOH, MeOH, rt, 20 min, 77%; (ii) ethylenediamine, rt, 2 h, 95%; (iii) 1,4-diaminobutane, rt, 2 h, 90%; (iv) MeNH2, HATU, DIPEA, DMF, rt, 12 h; (v) NH3/MeOH, rt, 12 h, 64% for steps iv and v; (vi) methylenebis(phosphonic dichloride), (CH3O)3PO, 0 °C, 3 h, 8–30%.