Synthesis of Nα-Z, Nβ-Fmoc or Boc protected α−hydrazinoacids and study of the coupling reaction in solution of Nα-Z-α-hydrazinoesters

Isabelle Bouillon (1) , Nicolas Brosse (1) , Régis Vanderesse (1) , Brigitte Jamart-Grégoire (1)

1 LCPM - Laboratoire de Chimie Physique Macromoléculaire

The preparation of chiral orthogonally protectedNa-Z,Nb-Fmoc- or Boc-a-hydrazinoacids derivatives, directly suitable for SPPS,is described in six steps with good yields starting from the correspondinga-aminoacids. The coupling reaction assays performed in liquidphase betweenNa-Z-hydrazinoesters andN-Fmoc-a-aminoacids demonstrated the low reactivity of the hydrazinoester derivatives. However,we found that the acid fluoride method allowed the formation of hydrazinodipeptides almost quantitatively

Domaines: Génie des procédés

Isabelle Bouillon, Nicolas Brosse, Régis Vanderesse, Brigitte Jamart-Grégoire. Synthesis of Nα-Z, Nβ-Fmoc or Boc protected α−hydrazinoacids and study of the coupling reaction in solution of Nα-Z-α-hydrazinoesters. Tetrahedron, 2007, 63, pp.2223-2234. ⟨10.1016/j.tet.2006.12.085⟩. ⟨hal-00198766⟩