Title:
NEW ACETOACETIC ESTER AND ITS PRODUCTION
Document Type and Number:
Japanese Patent JP2711244
Kind Code:
B2
Abstract:
PROBLEM TO BE SOLVED: To obtain the subject compound useful as an intermediate for synthesizing a starting substance for producing a β-lactam antibiotic such as a penem or carbapenem derivative.
SOLUTION: An acetoacetic acid ester represented by formula I is cyclized or acylated and then, isomerized with a base and subjected to hydrolysis, etc., to simply and inexpensively provide the objective 4-acyloxy-3-hydroxyethyl- azetidinone {(3R, 4R, 1'R)-4-acetoxy-3-(1'-hydroxyethyl)-2-azetidinone} represented by formula III and used as the starting substance in high total yield and stereoselectivity. The compound of formula I is obtained by reducing a compound represented by formula II using a bread yeast and converting the resultant compound. A protecting group is introduced into hydroxyl group and/or lactam nitrogen atom of the compound of formula III and then, the protected compound is reacted with mercaptan, etc., and the nitrogen atom is alkylated or acylated with an acetic acid derivative and a sulfur-containing 5-membered ring is closed to provide a β-lactam antibiotic.
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Inventors:
Peter Schneider
Gerald Ramos
Jack belzir
Gerald Ramos
Jack belzir
Application Number:
JP1381396A
Publication Date:
February 10, 1998
Filing Date:
January 30, 1996
Export Citation:
Assignee:
Novartis Actien Gezel Shaft
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): C07C229/22; C07D265/08; C12P13/00; C12P13/02
Other References:
ＣＨＥＭ．ＬＥＴＴ．〜７！，（１９８５），Ｐ．１０４５−１０４８
Attorney, Agent or Firm:
Hajime Tsukuni (1 person outside)