Premium
Syntheses of Phosphonic Esters of Alendronate, Pamidronate and Neridronate
Author(s) -
Guénin Erwann,
Monteil Maelle,
Bouchemal Nadia,
Prangé Thierry,
Lecouvey Marc
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200601067
Subject(s) - phthalimide , succinimide , chemistry , amino acid , alkyl , aryl , medicinal chemistry , organic chemistry , biochemistry
Several synthetic pathways for obtaining phosphonic esters of the amino bisphosphonic acids (NBPs) pamidronate, alendronate and neridronate were investigated. The general guideline was to react N ‐protected amino acids activated as phthalimide esters or as acyl chlorides. Succinimide esters were found less reactive and quickly abandoned. γ‐Lactam formation arises when starting from Boc‐ or Cbz‐protected amino acids. The phthalimide N ‐protecting group allowed access to alkyl or aryl mono‐, di‐ (symmetric or not) and triesters of these three NBPs in high yields. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)