Title:
PRODUCTION OF 4-SUBSTITUTED AZETIDINONE DERIVATIVE
Document Type and Number:
Japanese Patent JP3269867
Kind Code:
B2
Abstract:
PURPOSE: To obtain the subject compound useful as an intermediate for medicines such as a β-lactam-based antimicrobial agent in good yield by directly reacting a sulfide group of azetidinone derivative with an alkali metal compound in the presence of a copper compound without converting the sulfide group.
CONSTITUTION: An azetidinone derivative of formula I [OR1 is protected hydroxyl group; R2 is alkyl or (substituted)aromatic] is made to only react with an alkali metal compound of formula II [X is N, O or S; R3 is (substituted)alkyl, alkenyl, aralkyl, aryl or acyl; M is alkali metal, with proviso that when X is N, X forms a heterocyclic ring together with R3] in the presence of a copper compound [e.g. copper(I) oxide] to provide the objective 4-substituted azetidinone derivative of formula III [e.g. (3R, 4R)-3-[(R)-1-(tert.-butyldimethylsilyloxy) ethyl]-4-allyloxy-2-azetidinone]. The compound of formula II is obtained by reacting a compound of formula IV with an alkali metal hydride compound. This method is industrially advantageous, because the method is carried out in a short process, simple operation and good yield.
Inventors:
Masamichi Ishiguro
Takashi Nakatsuka
Rie Tanaka
Tetsuo Shimamoto
Takuro Yoshida
Hiromitsu Iwata
Takashi Nakatsuka
Rie Tanaka
Tetsuo Shimamoto
Takuro Yoshida
Hiromitsu Iwata
Application Number:
JP30814792A
Publication Date:
April 02, 2002
Filing Date:
October 21, 1992
Export Citation:
Assignee:
Suntory Limited
International Classes:
C07D205/08; C07D205/09; (IPC1-7): C07D205/09; C07D205/08
Domestic Patent References:
| JP3127773A | ||||
| JP3163057A |
Foreign References:
Attorney, Agent or Firm:
Taku Takeuchi