Title:
【発明の名称】4-アシルオキシ-3-ヒドロキシエチル-アゼチジノンの新規な製造方法
Document Type and Number:
Japanese Patent JP2520447
Kind Code:
B2
Abstract:
(3R,1'R)-4-Acyloxy-3-(1'-hydroxyethyl-2-azetidinones of the formula
in which R<1> is lower alkyl or aryl, are prepared in enantioselective reduction of the carbonyl group in a suitable alpha -acylaminomethylacetoacetic ester, cyclisation of the alpha -acylaminomethyl- beta -hydroxybutyric ester obtainable to give a 5,6-dihydro-1,3,4H-oxazine with inversion of the carbon atom carrying the hydroxyl group, equilibration to the preferentially trans-substituted dihydrooxazine, cleavage back to the alpha -aminomethyl- beta -hydroxybutyric acid of uniform configuration, ring-closure to the beta -lactam and oxidative acylation on C(4) of the beta -lactam. Compounds of the formula I can be used as starting materials for the preparation of beta -lactam antibiotics. Novel intermediates are also described.
Inventors:
PEETAA SHUNAIDAA
JERARUDO RAMOSU
JATSUKU BERUJIIRU
JERARUDO RAMOSU
JATSUKU BERUJIIRU
Application Number:
JP10776688A
Publication Date:
July 31, 1996
Filing Date:
May 02, 1988
Export Citation:
Assignee:
CIBA GEIGY
International Classes:
C12P13/00; C07C67/00; C07C227/00; C07C227/16; C07C227/18; C07C229/22; C07D205/08; C07D265/08; C07D499/06; C07D499/88; C07D499/897; C12P13/02; C12P17/10; C25B3/23; (IPC1-7): C07D205/08; C12P17/10; C25B3/02
Other References:
Ｓｔｕｄ．Ｏｒｇ．Ｃｈｅｍ．（Ａｍｓｔｅｒｄａｍ），３０（ＲｅｃｅｎｔＡｏｌｖ．Ｅｌｅｅｔｒｏｏｒｇ．Ｓｙｎｔｈ．），８９−９６（１９８７）
Attorney, Agent or Firm:
Hajime Tsukuni