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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
Notes
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Reaction equation

HRID 727610 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fc63eefa9a7f42d6afc7daea15c1f532
Source dataset
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05712267

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes