Isomerization and hydrolysis of chlorphenesin carbamate under strongly alkaline pH condition256 and epimerization and hydrolysis of carumonam (Fig. 15 ) 257 and moxalac-tam160161 all appear to conform to this model. Hydrolysis of chlorothiazide, under alkaline pH conditions,258 is explained by this model when k3 is set to zero (Fig. 16).

A more recent example is the aqueous degradation of the neuraminidase inhibitor prodrug GS-4104, which, like chlorphenesin carbamate, undergoes an acyl migration and hydrolysis.259 In the case of GS-4104, products P2 and P3 are also capable of interconverting as in the scheme below.

Figure 15. Time courses of epimerization and hydrolysis of cazumonam (pH 9.50, 35°C). (Reproduced from Ref. 257 with permission.)
Figure 16. Time course of hydrolysis of chlorothiazide ([OH-] = 0.1V 80°C). (Reproduced from Ref. 258 with permission.) Pseudo-First- and Pseudo-Second-Order Parallel Reactions

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