C - Chemistry – Metallurgy – 07 – F
Patent
C - Chemistry, Metallurgy
07
F
260/335.5
C07F 9/65 (1980.01)
Patent
CA 1164004
ABSTRACT OF THE DISCLOSURE The present invention provides a process for making novel intermediates of the formula Image II wherein Y is hydrogen, ethyl or .alpha.-hydroxyethyl; Q is phenyl or (lower) alkyl, R" is an easily removable ester protecting group and T is -?-X wherein X is -Alk)-A-(Alk')-R20, in which Alk represents a C1 - C2 alkylene group optionally substituted by a C1 - C4 alkyl radical; A is O, S, SO, SO2 or NR21 in which R21 is hydrogen, (lower) alkyl, phenyl or phenyl (lower) alkyl; Alk' is a C2 - C4 alkylene group; and R20 is a polar substituent selected from the group consisting of -NHOH, -NR22R23 in which R22 and R23 are each independently hydrogen or (lower) alkyl and -NO2; comprising a process chosen from: (a) reacting a compound having the formula Image with P(Q)3 in the presence of a base; or (b) reacting Image wherein M is a heavy metal, with X??, an acylating agent. These intermediates are useful for preparing 2-substituted and 2,6-disubstuted penem compounds of the formula Image wherein Y is hydrogen, halo or certain organic radicals and X represents certain hetero-interrupted substituted alkyl radicals,which are potent broad-spectrum antibacterial agents.
412517
Martel Alain
Menard Marcel
Bristol-Myers Squibb Company
Gowling Lafleur Henderson Llp
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