On the Solvolysis Kinetics of Amidoesters Derived from β-Aminoalcohols
To better understand reactivity in such systems, fifteen amidoesters derived from β-aminoalcohols were solvolyzed at the ester group in mildly basic methanol-d 4. All trials showed pseudo-first-order kinetics by 1H NMR. The rate constants are about 2 to 140-fold larger than those found with simple alkyl esters. The least bulky N-acyl groups generally sponsor the largest rate constants, and strongly so in two cases, but apparently not as a result of lesser steric crowding between the amide and ester groups. Rate constants are also greater for those amidoesters favoring an anti conformation at the amide linkage.
Hankins JN, Gouws M, Mahajer A, Kim ES, Gwaltney KP, Haseltine J. 2012. On the solvolysis kinetics of amidoesters derived from β-aminoalcohols. Tetrahedron Letters: International Organ for the Rapid Publication of Preliminary Communications in Organic Chemistry 53(19):2450-3.