NEW MATERIAL:A compound shown by formula I [R1 is lower alkyl, (protected) hydroxy lower alkyl; COOR2 is (protected) carboxyl or carboxylate anion; R3 and R4 are H or lower alkyl; n is 1-3]. EXAMPLE:Sodium (1R,5S,6S,8R)-6-(1-hydroxyethyl)-2-{[(2S,4S)-2-(3-oxopiperazin-1- yl)carbonylpyrrolidin-4-yl]thio)-1-methylcarbapenem-3-carboxylate. USE:An antimicrobial agent effective even to resistant microorganisms. PREPARATION:A compound shown by formula II is treated with diphenylphosphoryl chloride to give an intermediate shown by formula III. Then the intermediate and a thiol compound shown by formula IV are subjected to rearrangement reaction.
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