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In this study, the formation and stability of these key active esters were investigated with time-resolved H-1 NMR by using the common PyBOP/DIEA and HOBt/DIC coupling reagents for both alpha- and beta-amino acids. Parallel to the amide bond formation, the hydrolysis of the alpha/beta-active esters, a side reaction that is a considerable efficacy limiting factor, was studied. Based on the chemical nature/constitution of the active esters, three amino acid categories were determined: (i) the rapidly hydrolyzing ones (t < 6 h) with smaller (Ala) or even longer side chains (Arg) holding a large protecting group; (ii) branched amino acids (Ile, Thr) with slowly hydrolyzing (6 < t < 24 h) propensities, and (iii) non-hydrolyzing ones, such as the hard-to-couple beta-amino acids or beta-sugar amino acid derivatives, stable for longer times (t > 24 h) in solution. 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