Chymotrypsin mimics were synthesized by molecular imprinting technique using the transition state analogue phenyl-1-benzyloxycarbonylaminobenzyl phosphonate as the template, methacryloyl-L-histidine, and methacrylic acid as the functional monomers and EGDMA as the crosslinking agent. The TSA imprinted polymers were prepared in different porogens. Amidolysis of phenylalanine-p-nitroanilide was carried out using these TSA imprinted macromatric polymer catalysts. The investigations revealed that the porogen used in the polymerization reaction has a significant influence on the catalytic activity of the enzyme mimics in the amidolytic reactions. Morphological features of the polymer catalysts synthesized using DMSO and chloroform as the medium of polymerization were different. The macroporous polymer prepared in DMSO exhibited higher imprinting efficiency, enantioselectivity, and substrate shape specificity in amidolytic reactions compared to the less porous polymer catalyst prepared in chloroform. Pseudo first order kinetics was observed for the catalytic amidolysis.