On the Solvolysis Kinetics of Amidoesters Derived from β-Aminoalcohols

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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.