Acid-induced atypical spontaneous conversion of 5-amino-2,6-dioxooctahydro-1H-pyrrolo[2,1-d][1,5]oxazocine into 4-(hydroxymethyl)-2,5-dioxooctahydro-1H-pyrrolo[1,2-d][1,4]diazepine

Acid-induced atypical spontaneous conversion of... (5S,8S,10aR)-tert-butyl 5-(tert-butoxycarbonylamino)-2,6-dioxooctahydro-1H-pyrrolo[2,1-d][1,5]oxazocine-8-carboxylate 5, containing an original proline-like moiety, was prepared through Yamaguchi lactonization. However, it was observed that this 8 + 5 bicyclic lactone was spontaneously rearranged to the corresponding 7 + 5 bicyclic lactam under acid conditions, used to remove the Boc/tBu protecting groups. Both core structures were confirmed by one-dimensional and two-dimensional NMR, as well as HRMS. The new proline-like moieties are unknown up to now, and the 7 + 5 bicyclic lactam, much more stable than its precursor, may represent a valuable template to develop constrained non-peptide mimetics. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Research on Chemical Intermediates Springer Journals

Acid-induced atypical spontaneous conversion of 5-amino-2,6-dioxooctahydro-1H-pyrrolo[2,1-d][1,5]oxazocine into 4-(hydroxymethyl)-2,5-dioxooctahydro-1H-pyrrolo[1,2-d][1,4]diazepine

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Publisher
Springer Netherlands
Copyright
Copyright © 2014 by Springer Science+Business Media Dordrecht
Subject
Chemistry; Catalysis; Physical Chemistry; Inorganic Chemistry
ISSN
0922-6168
eISSN
1568-5675
D.O.I.
10.1007/s11164-014-1805-4
Publisher site
See Article on Publisher Site

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