P. S. Manchand was first to report boron trichloride as a reagent for hydrolysis of esters, inspired by this a modified procedure for the hydrolysis of methyl ester moiety in 18 under strictly anhydrous conditions was devised (Scheme 4), which successfully hydrolysed some of the methyl ester moiety in 18, leaving some of the hydrazone moiety in the thus obtained carboxylic acid 12 intact; however, some of the hydrazone moiety in 12 was also hydrolysed as well, the difficulty in achieving a satisfactory chemoselective ester hydrolysis via boron trichloride for 18 brings home to us the fact that the degree of success with which boron trichloride could or could not furnish a clean chemoselective ester hydrolysis for esters of this kind e.g. 18, is determined solely by the following variables: Initially, an anhydrous reaction condition was employed for hydrolysis of 18, in virtue of presumptions that boron trichloride activates the carboxyl moiety, in a manner similar to Acid-catalysed, alkyl-oxygen cleavage, unimolecular (A AL 1) with a positive value of ΔS ǂ i.e. dissociative, as opposed to commonly observed Basecatalysed, acyl-oxygen cleavage, bimolecular (B AC 2) with a negative value of ΔS ǂ i.e. associative, with nucleophiles of the general type Nu e.g. HO in saponification of uncomplicated esters, thus the aforementioned hydrolysis with boron trichloride could, in theory, take place in the absence of water, even though by definition the carboxyl ester hydrolysis is not hydrolysis without water. Support for the above view is provided by LC-MS analysis (Fig. ), such that 12 was formed upon contact of the thus obtained crude species from the action of boron trichloride on 18 under anhydrous conditions, with water under the LC-MS condition, which was not sufficient both in strength and time for the obtained carboxylic acid 12 to completely fall apart, and crucial evidence for its existence was brought to light. It should, however, be emphasised that the desired NInC 12 is partially zwitterionic in character, and this full-blown charge distribution, by all means, not only renders its purification by flash column chromatography infeasible, but also portrays its flash column chromatography purification as being far from ambitious. Nevertheless, attempts at flash column chromatography purification of crude 12 all failed, and preparative RP-HPLC had to be recruited. Moreover, it should not be overlooked that the desired NInC 12 is still inherently unstable in water or polar solvents such as methanol etc., and whilst the unreacted 18 was recovered in excellent purity by RP-HPLC purification, the desired NInC 12 was again hydrolysed this time to hydrazide 19, as evidenced by both LC-MS, and H NMR (ESI S49 †).