87746-57-4Relevant academic research and scientific papers
Solventless mechanosynthesis of N-protected amino esters
Konnert, Laure,Lamaty, Frederic,Martinez, Jean,Colacino, Evelina
, p. 4008 - 4017 (2014/05/20)
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.
Soluble alpha-amino acid salts in acetonitrile: practical technology for the production of some dipeptides.
Palomo, Claudio,Palomo, Antonio L,Palomo, Francisco,Mielgo, Antonia
, p. 4005 - 4008 (2007/10/03)
Alpha-amino acids are soluble in acetonitrile when treated with phosphazene bases. As a result, the protection/deprotection events that are usually required for peptide coupling reactions can be minimized. This is illustrated in the synthesis of the important angiotensin-converting enzyme (ACE) inhibitor enalapril. [reaction: see text]
