1,1'-Carbonyldiimidazole (CDI, Entry 4) resulted in a low yield of 10% of amide 9, and the process was also accompanied by the self-condensation of 1. Neither the amide synthesis from the ethyl ester derivative of 1 (Entry 5), nor the combination of EDC with 4-dimethylaminopyridine (DMAP, Entry 6), resulted in the formation of any product, leaving mostly unreacted starting materials or their mixture with some unidentified by-products, respectively. Nonetheless, the highest yield of amide 9 (88-92% by 1 H NMR) was attained with the EDC reagent (Entries 7-9). Nearly complete conversion of the starting materials and absence of by-products allowed the isolation of essentially pure amide 9 with 87-89% yields by following a simple work-up protocol, which involved washing with water, filtration, and drying. By focusing on a green chemistry-inspired amendment of the method, the hazardous LAG solvent nitromethane from the original protocol was replaced with the safer ethyl acetate. Notably, milling of 1 with EDC, without amine 8, resulted in the almost exclusive formation of the respective anhydride 1a. This result indicates that EDC-activated 1 is not inclined to rapid reaction with alcohols, in contrast to activation with CDI and COMU. for producing ester 9a through the reaction of 9 with 1 (see Table ). Both the COMU/K2HPO4 and TCFH/NMI systems yielded 9a at moderate yields of 31% and 40%, respectively (Table , Entries 1 and 2). These reagents have recently been shown to be effective for ester synthesis in solution and under mechanochemical conditions. However, using TCFH/K2HPO4 or EDC•HCl (Entries 3 and 4) resulted in only trace amounts of 9a, with the predominant process being the generation of anhydride 1a. In summary, the data presented in Tables and suggest that the COMU/K2HPO4 and TCFH/NMI systems are equally apt for the synthesis of both esters and amides.