title: Solventless mechanosynthesis of N-protected amino esters.
abstract: Mechanochemical derivatizations of N- or C-protected amino acids were performed in a ball mill under solvent-free conditions. A vibrational ball mill was used for the preparation of N-protected α- and β-amino esters starting from the corresponding N-unmasked precursors via a carbamoylation reaction in the presence of di-tert-butyl dicarbonate (Boc2O), benzyl chloroformate (Z-Cl) or 9-fluorenylmethoxycarbonyl chloroformate (Fmoc-Cl). A planetary ball mill proved to be more suitable for the synthesis of amino esters from N-protected amino acids via a one-pot activation/esterification reaction in the presence of various dialkyl dicarbonates or chloroformates. The spot-to-spot reactions were straightforward, leading to the final products in reduced reaction times with improved yields and simplified work-up procedures.
authors.affiliation: Institut des Biomolécules Max Mousseron , UMR 5247 CNRS-UM I-UM II, Place E. Bataillon, cc 1703, 34095 Montpellier, France.
authors.forename: Laure
authors.initials: L
authors.lastname: Konnert
authors.forename: Frédéric
authors.initials: F
authors.lastname: Lamaty
authors.forename: Jean
authors.initials: J
authors.lastname: Martinez
authors.forename: Evelina
authors.initials: E
authors.lastname: Colacino
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D004952:Esters / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D012997:Solvents / Q000737:chemistry
chemical_list: D000596:Amino Acids; D004952:Esters; D012997:Solvents