Synthesis and characterization of nateglinide derivatives

A series of seven nateglinide analogues were synthesized successfully using 4-isopropyl cyclohexyl carboxylic acid (trans acid) as starting material, react with thionyl chloride and formed trans-4-isopropyl cyclohexane carbonyl chloride (trans acid chloride) as an intermediate which further reacted with D-phenylalanine to yield nateglinide. The derivatives were synthesized by reacting nateglinide and ethylchloroformate, and formed an unstable mix anhydride compound, which further react with primary and secondary amines to yield the nateglinide derivatives. All these molecules were characterized spectroscopically by mass spectra, IR, 1H NMR.