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One pot synthesis and conformation of N-t-butyloxycarbonyl, O-Phenacyl derivatives of proline and other secondary amino acids

✍ Scribed by John Hondrelis; Greg Lonergan; Stavros Voliotis; John Matsoukas

Publisher: Elsevier Science
Year: 1990
Tongue: French
Weight: 673 KB
Volume: 46
Category: Article
ISSN: 0040-4020
DOI: 10.1016/s0040-4020(01)85437-5

No coin nor oath required. For personal study only.

✦ Synopsis

Proline, 4-hydroxyproline, azetidine-2-carboxylic acid, pipecolic acid and proline containing dipeptides were converted to N-t-butyloxycarbonyl, 0-phenacyl derivatives in a one pot synthesis. 'H-and 13C-NMR spectroscopy of certain derivatives (Boc-Pro-PE, Boc-4Hyp-PE, Boc-Pro-4BrPE and Boc-Pip-PE) in CDC13 solution reveal the presence of cis-trans isomers in almost equal quantities. On the contrary, the 'Ii-and 13C-NMB spectra of the N-t-butyloxycarbonyl phenacyl ester of azetidine-2-carboxylic acid, show the presence of one isomer only. Similarly, only one urethane isomer was observed in solution for the protected C-terminal angiotensin II dipeptides, N-t-Boc-Pro-Phe-PE and N-t-Boc-Pro-Ile-PE. All phenacyl derivatives exhibited magnetic asymmetry attributed to steric factors.

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