A simple synthesis of N β-Fmoc/Z-amino alkyl thiols and their use in the synthesis of N β-Fmoc/Z-amino alkyl sulfonic acids

A simple and efficient protocol for the synthesis of Nβ- Fmoc/Z-amino alkyl thiols is described. The approach uses sodium pyrosulfite-mediated hydrolysis of isothiouronium salts resulting from the reaction between N-protected aminoalkyl iodides and thiourea. N-Protected taurines were prepared through performic acid oxidation of the thiols and the products were further utilized for the synthesis of dipeptidosulfonamides. © Georg Thieme Verlag Stuttgart - New York