NEW MATERIAL:A compound of formula I [X is methylene, ethylidene or S; R1 is formula II (R2 is H, F, etc.; R3WR5 are H, lower alkyl or cycloalkyl, etc., provided that R2WR5 do not represent H at the same time, at least one has F, at least one of R3WR5 represents lower alkenyl or alkynyl], formula III (Y is a joint bond of a ring structure and alkylene, etc. containing 2W5 ring constituent atoms of C, O, S or N), etc.].
EXAMPLE: ( 5R,6S )-2-( N-2-Fluoroethylcarbamidoylmethylthio )-6-( 1-R-hydroxyethyl)-2-carbapenem-3-carboxylic acid.
USE: An antimicrobial agent having inhibitory activity against β-lactamases.
PREPARATION: A compound of formula IV (R6 is H or methyl. R7 is a protecting group of the carboxyl group) is reacted with an alkanesulfonic acid anhydride, etc. in the presence of a base, and the resultant reaction product is reacted with a mercaptan of the formula HS-R1. The protecting group R7 is then removed.
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