Synthesis X-ray crystallography and antimicrobial activity of protected and deprotected amides

Twenty four chiral protected and deprotected amides were synthesized by using commercially available l-tartaric acid,having two asymmetric centers and c2 axis of symmetry. in the synthetic sequence,diacid functionality of l-tartaric acid was protected as dimethyl ester and dihydroxy groups as acetonoid. the partial hydrolysis of acetonoid of dimethyl ester gives the corresponding monoesters. monoester upon treatment with different substituted aromatic amines gave desired amides (1a-1l). amides (1a-1l) afforded compounds (2a-2l) after reacting with acetyl chrloride and methanol. all the compounds were purified and characterized by using sophisticated spectroscopic techniques including ir,1h-nmr,13c-nmr and elemental analysis. the structure of compounds 1a and 2l were unambiguously obtained by x-ray crystallography. protected (1a-1l) and deprotected amides (2a-2l) were tested for their antimicrobial activities at different concentrations against different strains of bacteria and fungi and found to be antimicrobial.