Hydrochloric Acid → (1R,5S,6S)-2-[(2S,4S)-2-(3-Aminoazetidin-1-yl-carbonyl)pyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid hydrochloride

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Reaction Steps

216 mg of 4-nitrobenzyl (1R,5S,6S)-2-((2S,4S)-2-[3-(4-nitrobenzyloxycarbonylamino)azetidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-ylthio)-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate [prepared as described in step (1) above] were dissolved in 10 ml of a 3:2 by volume mixture of tetrahydrofuran and water. 250 mg of a 10% w/w palladium-on-carbon catalyst and 239 μl of 1N aqueous hydrochloric acid were then added to the resulting solution, after which the mixture was hydrogenated at room temperature for 1.5 hours in an atmosphere of hydrogen. At the end of this time, the catalyst was removed by filtration, and the filtrate was washed with diethyl ether. The aqueous phase was then concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography (Cosmosil 75C18 -prep, manufactured by Nacalai Tesque, 18 ml). Of the fractions obtained by elution with water, the one containing the title compound was concentrated by evaporation under reduced pressure and freeze-dried to give 46 mg of the title compound as a powder.

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