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. 2023 Apr 26;66(9):6391–6402. doi: 10.1021/acs.jmedchem.3c00415

Scheme 9. Synthesis of Carboxylic Acid Bioisosteres 1318.

Scheme 9

Reagents and conditions: (a) NH4Cl, EDC, 4-DMAP, DMF, 70 °C, 8 h, 35%; (b) NH2OH·HCl, CDI, THF, rt, 8 h, 74%; (c) NHMeOH·HCl, CDI, THF, rt, 1 h, 8%; (d) NH2OMe, DCC, DMAP, NEt3, CH2Cl2, 60 °C, 8 h, 14%; (e) NH2CN, HATU, NiPr2Et, DMF, rt, 8 h, 22%; (f) NH2SO2Me, DCC, DMAP, NEt3, CH2Cl2, 60 °C, 8 h, 12%.