1027750-52-2Relevant academic research and scientific papers
Synthesis of β,β′-diamino acids from α-amino acid-derived β-lactams by ring opening with nucleophiles. Utilization in the synthesis of peptidomimetics
Taubinger, Alexander A.,Fenske, Dieter,Podlech, Joachim
, p. 8659 - 8667 (2008/12/21)
Ring opening of protected 3-aminoalkyl-substituted azetidin-2-ones with O-, N- or S-nucleophiles led to β,β′-diaminocarboxylic esters, amides and thioesters, respectively. The reaction outcome is improved by the addition of catalytic amounts of sodium azide. Utilization of a glycine derivative with unprotected amino function as nucleophile was possible. When bulkier amino acid esters were used, the intermediate acid azide underwent a Curtius rearrangement. The isocynates formed were trapped as the corresponding urea derivatives. Reduction of β-lactam's amide moiety led to diaminoalcohols.
