Intermediates for cephalosporin analogues

Details Intermediates for cephalosporin analogues Intermediates for cephalosporin analogues

C - Chemistry, Metallurgy

07

D

260/300, 260/385

C07D 205/08 (2006.01) C07D 205/085 (2006.01) C07D 505/00 (2006.01) C07F 9/568 (2006.01)

Patent

CA 1076125

ABSTRACT The present invention relates to novel intermediates useful in the synthesis of 1-oxacephalporins which are represented by the formula: Image wherein A is amino or substuted amino; COB is carboxy or protected carboxy; X is halogen or group OR (in which R is a group represented by the formula: -CH2CH?CH, -CH2C?CNU, -CH2CH?CH2 , -CH2COCH3, Image , Image , Image Image , or -CH2COCH2Nu in which Nu is a nucleophilic group selected from the group consisting of: hydroxy, acyloxy derived from (C1 to C10)-organic acids or inorganic acids, (C1 to C10)-alkoxy, mono- or di-cyclic carbo- or hetero-cyclic aralkoxy, and monocyclic carbo- or hetero-cyclic aryloxy; mercapto, acylthio derived from (C1 to C10) organic acids or inorganic acids (C1 to C10)alkylthio, mono-or di-cyclic carbo- or hetero-cyclic aralkylthio, and mono or dicyclic carbo- or hetero cyclic arylthio; amino, azido, hydrazo, acylamino derived from (C1 to C12)organic or inorganic acids, (C1 to C5)alkylamino, mono- or di-cyclic carbo- or hetero-cyclic aralkylamino or arylamino or halogen); R1 is a group of the formula: =C(CH3)2, = O, Image , Image , or = PR23 (in which Hal is halogen or alkylsulfonyloxy, and R2 is alkyl or aryl); and Y is hydrogen or methoxy; provided that when R is propargyl or -CH2COCH3 and R1 is Image , Image , or = PR23 A is at the 3.alpha.-position and Y is 3.beta.-hydrogen, or A is at the 3.beta.-position and Y is a 3.alpha.-methoxy, and a process for their preparation.

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