Synthesis of (2S)-2-(benzoylamino)-3-(heteroaryl)propyl benzoates

Authors
Skof, M Svete, J Stanovnik, B Golic-Grdadolnik, S
Citation
M. Skof et al., Synthesis of (2S)-2-(benzoylamino)-3-(heteroaryl)propyl benzoates, HELV CHIM A, 83(4), 2000, pp. 760-766
Citations number
34
Categorie Soggetti
Chemistry & Analysis",Chemistry
Journal title
HELVETICA CHIMICA ACTA
ISSN journal
0018019X → ACNP
Volume
83
Issue
4
Year of publication
2000
Pages
760 - 766
Database
ISI
SICI code
0018-019X(2000)83:4<760:SO(B>2.0.ZU;2-B
Abstract
(3E,5S)-1-Benzoyl-5-[(benzoyloxy)methyl]-3-[(dimethylamino)methylidene]pyrr olidin-2-one (9) was prepared in two steps from commercially available (S)- 5-(hydroxymethyl)pyrrolidin-2-one (7) (Scheme 1). Compound 9 gave. in one s tep, upon treatment with various C,N- and C,O-1,3-dinucleophiles 10-18, the corresponding 3-(quinolizin-3-yl)- and 3-(2-oxo-2H-pyran-3-yl)-substituted (2S)-2-(benzoylamino)propyl benzoates 19-27 (Schemes 1 and 2).