Patent ID: 7064199
Filing Date: 2006-06-20
Classification: C07D,Y02P

Abstract:
1. A process for producing a vinylpyrrolidinone-cephalosporin derivative of formula A-1 wherein * denotes a center of chirality; comprising: (a) converting a compound of the formula II wherein X is a protected hydroxy group; Z wherein Z (b) reducing said N-hydroxy derivative of formula III to the secondary amine derivative of formula IV wherein Z (c) converting said secondary amine of formula IV into a 3-amino pyrrolidine compound of formula I wherein R (d) reacting said 3-amino-pyrrolidine compound of formula I with 2-bromo-4-chlorobutanoylchloride to yield a compound of formula (1) wherein R (e) converting said compound of formula (1) into the corresponding triphenylphosphine Wittig salt of formula (2) wherein Ph is phenyl and R (f) reacting said Wittig salt of formula (2) with a diprotected 3-ene cephalosporin derivative of formula (3) wherein BOC is tert.-butoxycarbonyl; and Ph is phenyl; to yield the condensation product (4) wherein *, BOC, R (g) oxidizing said condensation product of formula (4) to produce the 5-sulfoxide compound of formula (5) wherein *, R (h) reducing the sulfoxide group on said 5-sulfoxide compound of formula (5) to form the 2-ene celphalosporin derivative of formula (6) wherein *, BOC and Ph are as above. (i) deprotecting the 7-amino group of said compound of formula (6) and acylating the deprotected compound of formula (6) with (Z)-(5-amino[1,2,4]thiadiazol-3-yl-trityloximino-thioacetic acid S-benzothiazol-2-yl ester to yield the compound of formula (1) wherein *, R (j) removing the protecting amino protecting groups R