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. 2016 May 11;21(5):615. doi: 10.3390/molecules21050615

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© 2016 by the authors.

Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).

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Scheme 11 — Synthetic scheme for generating N^G-(2-methoxyethyl)-l-arginine carboxylate bioisosteres. Reagents and Conditions: (i) i-BuCOCl, N-methylmorpholine, NH₄OH (30%), THF, −10 °C-RT, 3 h, 99%; (ii) TFAA, TEA, THF, 0 °C-RT, 16 h, 47%; (iii) 4 M HCl/1,4-dioxane, DCM, RT, 30 min, 99%; (iv) DIPEA, DCM, RT, 24 h, 40%; (v) NaN₃, ZnBr₂, H₂O/2-propanol, reflux, 16 h, 30%; (vi) (1) NH₂OH·HCl, NaHCO₃, DMSO, reflux, 16 h; (2) CDI, DBU, THF, reflux, 30 min, 73%; (vii) TFMSA/TFA, DCM, RT, 30 min, 99%. Reproduced in part from [117] with permission of the Royal Society of Chemistry.