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

A solution of 1.3 of 4-nitrobenzyl (1R, 5S, 6S)-2-[(2S, 4S)-2-[4-(4-nitrobenzyloxycarbonyl)-1-homopiperazinylcarbonyl]-1-methylpyrrolidin-4-ylthio]-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate [prepared as described in step (a) above] in 20 ml of a 1:1 by volume mixture of tetrahydrofuran and water was mixed with 2.6 ml of 1N aqueous hydrochloric acid, and the mixture was hydrogenated by bubbling hydrogen through it at room temperature for 2 hours in the presence of 10% w/w palladium-on-charcoal. The catalyst was then removed by filtration, and the filtrate was washed with diethyl ether. The aqueous solution was concentrated by evaporation under reduced pressure, after which the reside was purified by reverse phase column chromatography through a Labar column (Merck, LiChroprep RP-8, size B), using water as the eluent. Those fractions containing the title compound were collected, concentrated by evaporation under reduced pressure and lyophilized, to give 260 mg of the title compound as a powder.

1. customby bubbling hydrogen through it at room temperature for 2 hours in the presence of 10% w/w palladium-on-charcoal
2. customThe catalyst was then removed by filtration
3. washthe filtrate was washed with diethyl ether
4. concentrationThe aqueous solution was concentrated by evaporation under reduced pressure
5. customafter which the reside was purified by reverse phase column chromatography through a Labar column (Merck, LiChroprep RP-8, size B)
6. additionThose fractions containing the title compound
7. customwere collected
8. concentrationconcentrated by evaporation under reduced pressure

ORDレコード

ord-1197a124bafd4e2c8d5685b1f254c675

出典データセット

uspto-grants-1999_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05866564