HCID 178418361, compound → HCID 178480886, compound

HRID 1613998Notes

Reaction equation

HRID 1613998 reaction equation
[I-].O[C@@H]([C@H:5]1[C:11](=[O:12])[N:10]2[C@@H:6]1[C@@H:7](C)[C:8]([S:26][C@@H:27]1[CH2:31][N:30](C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[C@H:29]([CH2:45][N+:46]3[CH:50]=[CH:49][N:48]([CH3:51])[CH:47]=3)[CH2:28]1)=[C:9]2[C:13]([O:15]CC1C=CC([N+]([O-])=O)=CC=1)=[O:14])C.[H][H]>O1CCCC1.P([O-])([O-])([O-])=O.[OH-].[OH-].[Pd+2]>[CH3:51][N:48]1[CH:49]=[CH:50][N+:46]([CH2:45][C@@H:29]2[CH2:28][C@H:27]([S:26][C:8]3[CH2:7][CH:6]4[N:10]([C:11](=[O:12])[CH2:5]4)[C:9]=3[C:13]([O-:15])=[O:14])[CH2:31][NH:30]2)=[CH:47]1

Participants

6

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178462282HCID 178462282, compound

Product 1

HCID 178480886HCID 178480886, compoundYield 77.1%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 1061PhosphateSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitrobenzyl (4R,5S,6S)-6-[(lR)-1-hydroxyethyl]-4-methyl-3-[(2S, 4S)-2-(3-methyl-1-imidazolio)methyl-1-4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-7-oxo -1-azabicyclo-3.2.0]hept-2-ene-2-carboxylate iodide (0.79 g) obtained in Example 3-1) in a mixture of tetrahydrofuran (50 ml) and 0.1 M phosphate buffer (pH 6.5) (50 ml) was stirred in the presence of 20 % palladium hydroxide on carbon (0.3 g) under atmospheric pressure of hydrogen at ambient temperature for 5 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to remove the tetrahydrofuran. The residual solution was washed with ethyl acetate (50 ml ×2) and the organic solvent was removed by evaporation. The equeous solution was subjected to a column chromatography on nonionic adsorption resin, "Diaion HP-20" (50 ml), washed with water, eluted with a mixture of acetone and water (1:99 V/V). The fractionscontaining the desired compound were collected and lyophilized to give (4R,5S,6S)-6-[(lR)-1-hydroxyethyl]4-methyl-3-[(2S,4S)-2-(3-[(2S,4S)-2-(3-methyl-1-imidazolio)methylpyrrolidin-4-yl]thio-7-oxo-1-azabicyclo [3.2.0]hept-2-ene-2-carboxylate (0.25 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto remove the tetrahydrofuran
  4. washThe residual solution was washed with ethyl acetate (50 ml ×2)
  5. customthe organic solvent was removed by evaporation
  6. wash" (50 ml), washed with water
  7. washeluted with a mixture of acetone and water (1:99 V/V)
  8. customThe fractionscontaining the desired compound were collected

Sources & evidence

ORD record
ord-28e17b1937d742a5b1ced13e6cc23eb4
Source dataset
uspto-grants-1993_03
Patent number
US05194624

Reaction notes

Loading…