ChemInform Abstract: Synthesis of Functionalized Non‐Natural Amino Acid Derivatives via Amidoalkylation Transformations.

Abstract

ChemInform Abstract Two different synthetic approaches to amino acid amides bearing a (hetero)aryl substituent in the α-position are examined. Treatment of the 2-acetamido-2-methoxyacetate (I) with furan (II) or pyrrole (IV) in the presence of boron trifluoride etherate gives the functionalized α-amino esters (III) or (V) and (VI). (III) is converted to the benzylamide (VIIIc) by conventional methods. Better results are achieved when the acetamidoethoxyacetate (IX) is first transformed into the benzamide (X) and the (het)aryl substitutent is introduced in the second step, producing (VIII).