Isolation of an amphoteric compound poses a unique challenge. Because the compound exists in its salt form at both high and low pH, only a narrow pH window exists where the compound can be isolated in its neutral form. This issue was resolved by addition of a buffer to robustly isolate the neutral form at production scale. Additionally, the acidic hydrolysis reaction to make this compound posed a challenge with a shift in equilibrium from its acid form to its ester form, decreasing yield and producing low quality material. The key to preventing this reversal was in the temperature at which the acid is quenched. A systematic approach to problem solving for a robust production process is discussed.
