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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

HRID 727610
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 727610
[N+](C1C=CC(COC([N:12]2[CH2:18][CH2:17][CH2:16][N:15]([C:19]([C@@H:21]3[CH2:25][C@H:24]([S:26][C:27]4[C@H:28]([CH3:51])[C@@H:29]5[C@@H:46]([C@H:47]([OH:49])[CH3:48])[C:45](=[O:50])[N:30]5[C:31]=4[C:32]([O:34]CC4C=CC([N+]([O-])=O)=CC=4)=[O:33])[CH2:23][N:22]3[CH3:52])=[O:20])[CH2:14][CH2:13]2)=O)=CC=1)([O-])=O.O1CCCC1.[ClH:60]>O>[ClH:60].[N:15]1([C:19]([C@@H:21]2[CH2:25][C@H:24]([S:26][C:27]3[C@H:28]([CH3:51])[C@@H:29]4[C@@H:46]([C@H:47]([OH:49])[CH3:48])[C:45](=[O:50])[N:30]4[C:31]=3[C:32]([OH:34])=[O:33])[CH2:23][N:22]2[CH3:52])=[O:20])[CH2:16][CH2:17][CH2:18][NH:12][CH2:13][CH2:14]1
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Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 1317204274-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

Produkt 1

HCID 67618866(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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of 1.3 g 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 residue was purified by reverse phase column chromatography through a Lobar 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.

Aufarbeitung

  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 residue was purified by reverse phase column chromatography through a Lobar column (Merck, LiChroprep RP-8, size B)
  6. additionThose fractions containing the title compound
  7. customwere collected
  8. concentrationconcentrated by evaporation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-fc63eefa9a7f42d6afc7daea15c1f532
Quelldatensatz
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05712267

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