合成路线1

Several improvements is the synthesis of 258849 have been developed: The reaction of stannatrane chloride (I) with Et2Zn and CH2I2 in HF gives iodomethylstannatrane (II), which is condensed with the naphthosultam (III) (intermediate (VII) in previous synthesis of 258849, scheme 25884901a) by means of K2CO3 in DMF yielding the stannatrane derivative (IV). The reaction of (IV) with Tf2O and lutidine in dichloromethane affords the corresponding ester (V), which is condensed with 1-(carbamoylmethyl)-4-aza-1-azoniabicyclo[2.2.2]octane trifluoromethanesulfonate (VI) (intermediate (XLV) in scheme 25884901g) giving the stannatrane derivative (VII). The condensation of intermediate (VII) with carbapenem triflate (VIII) (intermediate (XLI) in scheme 25884901f) by means of a Pd catalyst in acetonitrile provides the protected carbapenem derivative (IX) (intermediate (II) in scheme 25884902a). Finally, this compound is deprotected first with HCl to eliminate the silyl group and then with H2 over Pd/C to eliminate the p-nitrobenzyl group.