82212-43-9Relevant academic research and scientific papers
Simple method for benzamidomethylation of phenols in water solution
Popovski, Emil,Klisarova, Ljiljana,Vikic-Topic, Drazen
, p. 3451 - 3458 (2007/10/03)
Benzamidomethyl ethers ROCH2NHBz (5) (R = aryl, cyclohexyl and benzyl) were obtained in high yields in reactions of ROH (4) with (benzamidomethyl)triethylammonium chloride 3 as a benzamidomethylation agent. Reactions occurred in water, except r
Mechanism of Hydrolysis of Benzamidomethyl Derivatives of Phenols and Its Implications for Prodrug Design
Getz, John J.,Prankerd, Richard J.,Sloan, Kenneth B.
, p. 1702 - 1706 (2007/10/02)
A series of O-benzamidomethyl derivatives of phenols was synthesized, and their rates of hydrolysis were investigated.The hydrolyses of the compounds follow pseudo-first-order kinetics resulting in quantitative and rapid regeneration of the phenol.The rates of hydrolysis were shown to be dependent on phenol nucleofugicity as well as the pKa of the amide.The mechanism of hydrolysis apparently involves as elimination of the phenol anion from the conjugate base of the amide (E1cB-like).
