HCID 57148285, compound → HCID 67867051, compound

HRID 346386Notes

Reaction equation

HRID 346386 reaction equation
[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:62])[C:7]([S:25][C@@H:26]1[CH2:30][N:29](C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[C@H:28]([CH2:44][O:45][CH2:46][CH2:47][NH:48]C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[CH2:27]1)=[C:8]2[C:12]([O:14]CC1C=CC([N+]([O-])=O)=CC=1)=[O:13])[CH3:3].[H][H]>O1CCCC1.C([O-])(=O)C.[OH-].[OH-].[Pd+2]>[C:12]([OH:14])(=[O:13])[CH3:8].[NH2:48][CH2:47][CH2:46][O:45][CH2:44][C@@H:28]1[CH2:27][C@H:26]([S:25][C:7]2[C@H:6]([CH3:62])[C@H:5]3[N:9]([C:10](=[O:11])[C@@H:4]3[C@H:2]([OH:1])[CH3:3])[C:8]=2[C:12]([OH:14])=[O:13])[CH2:30][NH:29]1

Participants

6

Reactant 2

HCID 57148285HCID 57148285, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67867051HCID 67867051, compoundYield 46.5%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 175AcetateSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-{2-(4-nitrobenzyloxycarbonylamino)ethyloxymethyl}pyrrolidin-4-yl]thio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene 2-carboxylate (0.45 g) in a mixture of tetrahydrofuran (25 ml) and 0.2M acetate buffer (pH 5.8) (25 ml) was stirred in the presence of 20% palladium hydroxide on carbon (0.1 g) under atmospheric pressure of hydrogen at ambient temperature for 8 hours. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to remove tetrahydrofuran. The residual solution was washed with ethyl acetate (40 ml×2) and the organic solvent was removed by evaporation. The residual solution was subjected to a column chromatography on nonionic adsorption resin, "HP-20" (trademark, made by Mitsubishi Chemical Industries) (20 ml) and eluted with water. The fractions containing the desired compound were collected and lyophilized to give (4R,5S,6S)-3-[(2S,4S)-2-(2-aminoethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid acetate (0.053 g).

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto remove tetrahydrofuran
  4. washThe residual solution was washed with ethyl acetate (40 ml×2)
  5. customthe organic solvent was removed by evaporation
  6. washeluted with water
  7. additionThe fractions containing the desired compound
  8. customwere collected

Sources & evidence

ORD record
ord-3593768184f3474b9fd9cf9ae1174b29
Source dataset
uspto-grants-1991_10
Patent number
US05061804

Reaction notes

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