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Article Dans Une Revue Journal of Organic Chemistry Année : 2014

Solventless Mechanosynthesis of N‑Protected Amino Esters

Résumé

Mechanochemical derivatizations of N- or Cprotected 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.
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Dates et versions

hal-00990729 , version 1 (14-05-2014)

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Laure Konnert, Frédéric Lamaty, Jean Martinez, Evelina Colacino. Solventless Mechanosynthesis of N‑Protected Amino Esters. Journal of Organic Chemistry, 2014, 79 (9), pp.4008-4017. ⟨10.1021/jo500463y⟩. ⟨hal-00990729⟩
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