C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/298.2
C07D 498/04 (2006.01)
Patent
CA 1150270
ABSTRACT OF THE DISCLOSURE Described herein are oxazolinoazetidinones of formula (I): Image (I) wherein R is hydrogen or a carboxylic acid protecting group and R1 is (a) hydrogen, C1-C4 alkyl or halo(C1-C4 alkyl); (b) a group R6 wherein R6 is phenyl or phenyl substituted by 1 or 2 groups selected from the group consisting of fluoro, chloro, bromo, iodo, nitro, cyano, C1-C4 alkyl, C1-C4 alkoxy, protected hydroxy, carbamyl, tri- fluoromethyl and methanesulfonamido; (c) a group of the formula R6(O)mCH2- wherein m is 1 or 0 and R6 is as defined above (d) a group of the formula R6aCH2- wherein R6a is cyclohexadienyl, 2- furyl, 2-thienyl, or 3-thienyl; or (e) a group of the formula -COOR wherein R is as defined above. These compounds are prepared by cyclising a chloro- azetidinone compound of formula (II): Image (II) wherein R and R1 are as defined above. The aforesaid oxazolinoazetidinones of formula (I) are useful intermediates for the synthesis of oxygen analogues of penicillins.
354148
Goodson Theodore
Spitzer Wayne A.
Eli Lilly And Company
Gowling Lafleur Henderson Llp
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