Hydrochloric Acid → HCID 67619244, compound

HRID 362015Notes

Reaction equation

HRID 362015 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]([C@@H:12]2[CH2:16][C@H:15]([S:17][C:18]3[C@H:19]([CH3:42])[C@@H:20]4[C@@H:37]([C@H:38]([OH:40])[CH3:39])[C:36](=[O:41])[N:21]4[C:22]=3[C:23]([O:25]CC3C=CC([N+]([O-])=O)=CC=3)=[O:24])[CH2:14][N:13]2[CH3:43])=[O:11])[CH2:6][CH2:5]1.O1CCCC1.[ClH:49]>O>[ClH:49].[OH:1][CH2:2][CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:10]([C@@H:12]2[CH2:16][C@H:15]([S:17][C:18]3[C@H:19]([CH3:42])[C@@H:20]4[C@@H:37]([C@H:38]([OH:40])[CH3:39])[C:36](=[O:41])[N:21]4[C:22]=3[C:23]([OH:25])=[O:24])[CH2:14][N:13]2[CH3:43])=[O:11])[CH2:8][CH2:9]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 1317204294-Nitrobenzyl (1R,5S,6S)-2-{(2S,4S)-2-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl]-1-methylpyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate

Product 1

HCID 67619244HCID 67619244, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 700 mg of 4-nitrobenzyl (1R,5S,6S)-2-{(2S,4S)-2-[4-(2-hydroxyethyl)-1-piperazinylcarbonyl]-1-methylpyrrolidin-4-ylthio}-6-[(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylate [prepared as described in step (a) above] in 60 ml of a 1:1 by volume mixture of tetrahydrofuran and water was mixed with 1.15 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 1000 mg of 10% w/w palladium-on-charcoal. At the end of this time, the catalyst was removed by filtration, and the filtrate was extracted with diethyl ether. The remaining aqueous layer was concentrated by evaporation under reduced pressure, and the residue was subjected to column chromatography through a Lobar column (Merck, LiChroprep RP-8, size B). The column was eluted with 1.5% v/v aqueous methanol and those fractions containing the title compound were combined, concentrated by evaporation under reduced pressure and lyophilized, to give 300 mg of the title compound as a colorless powder.

Workup

  1. customby bubbling hydrogen through it at room temperature for 2 hours in the presence of 1000 mg of 10% w/w palladium-on-charcoal
  2. customAt the end of this time, the catalyst was removed by filtration
  3. extractionthe filtrate was extracted with diethyl ether
  4. concentrationThe remaining aqueous layer was concentrated by evaporation under reduced pressure
  5. washThe column was eluted with 1.5% v/v aqueous methanol
  6. additionthose fractions containing the title compound
  7. concentrationconcentrated by evaporation under reduced pressure

Sources & evidence

ORD record
ord-46fe952f49504960a5acef3161349a53
Source dataset
uspto-grants-1999_02
Patent number
US05866564

Reaction notes

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