A series of substituted anilinyl conjugates glu-CDCA were synthesized using two synthetic approaches. In the first approach (used for synthesis of all targets except 2 ) α-benzyl glutamic acid was first coupled to CDCA via either N-hydroxysuccinimide (OSU) ester or benzotriazole (OBT) ester. Various substituted aniline probes were then coupled to glutamic acid by stirring either at RT or 60°C using O-Benztriazol-1-yloxytris-1,1,3,3 tetra methyl uranium hexaflourophosphate (HBTU) as the activating agent and triethylamine (TEA) as the base. The resulting neutral compounds were then subjected to hydrogenation in parr shaker for 1-2 h in ethanol (EtOH) and 10% palladium to remove the α-benzyl group, yielding the mono and dianionic targets. To synthesize 2 (Scheme 2 ), a second approach was needed.
All neutral compounds intermediates were purified by column chromatography using a gradient of hexane and ethyl acetate. All final target compounds were obtained as solids after deprotection. Identity and purity were confirmed by TLC, MS, NMR, and elemental analysis. All final target compounds possessed ≥95% purity.
All neutral compounds intermediates were purified by column chromatography using a gradient of hexane and ethyl acetate. All final target compounds were obtained as solids after deprotection. Identity and purity were confirmed by TLC, MS, NMR, and elemental analysis. All final target compounds possessed ≥95% purity.
