Synthesis of thioureido peptidomimetics employing alkyl azides and dithiocarbamates

An unprecedented approach for the assembly of thioureido peptidomimetics is developed employing alkyl azides and dithiocarbamates. Dithiocarbamates react with alkyl azides with the liberation of N 2 and elemental sulfur thereby leading to thiourea in a traceless manner. Thioureido peptidomimetics are thus furnished in good yields with no epimerization. This process is mild, free from the use of a base, scalable and step economic. The practicability of this methodology has been highlighted by the synthesis of N , N ′-orthogonally protected thioureido peptidomimetics. An efficient and one pot protocol for the synthesis of thioureidopeptidomimetics is described.