Author/Editor		Časar, Zdenko; Japelj, Miha
Title		Sinteza N-(1-(S)-etoksikarbonil-3-okso-3-fenilpropil)-L-alanina
Type		članek
Source		In: Glavič P, Brodnjak-Vončina D, editors. Zbornik referatov s posvetovanja Slovenski kemijski dnevi 1998; 1998 sep 17-18; Maribor. Maribor: FKTT,
Publication year		1998
Volume		str. 226-31
Language		slo
Abstract		Title compound and some of its derivatives are intermediates for preparation of key synthons, which are used in the synthesis of selected ACE inhibitors. In the first part of our investigations synthesis of N-(1-( S )-ethoxycarbonyl-3-oxo-3-phenylpropyl)-L-alanine ( 7a ) was performed. In the fnst step the Friedl-Crafts acylation of benzene ( 1 ) with malefic anhydride ( 2 ) was carried out and traps-benzoylacrylic acid ( 3 ) was isolated. After esterification of ( 3 ) with etanol traps-etil 3-benzoylacrylate ( 5 ) was isolated. In the next step the Michael addition reaction of lithium salt of L-alanine ( 6 ) on the double bond of ( 5 ) was carried out, which gave a diastereoisomeric mixture of ( 7a ) and ( 7b ). Desired ( S, S )-diastereoisomer was isolated by selective crystallization.
Descriptors		ANGIOTENSIN-CONVERTING ENZYME INHIBITORS DRUG INDUSTRY CHEMISTRY, PHARMACEUTICAL