HCID 86744489, compound → HCID 67929791, compound

HRID 703599Notes

Reaction equation

HRID 703599 reaction equation
[CH3:1][N:2]([CH3:51])[CH2:3][CH2:4][O:5][CH2:6][C@@H:7]1[CH2:11][C@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H:21]([OH:23])[CH3:22])[C:14]=2[C:25]([O:27]CC2C=CC([N+]([O-])=O)=CC=2)=[O:26])[CH2:9][N:8]1C(OCC1C=CC([N+]([O-])=O)=CC=1)=O.[H][H]>O1CCCC1.C([O-])(=O)C.[OH-].[OH-].[Pd+2]>[C:25]([OH:27])(=[O:26])[CH3:14].[CH3:51][N:2]([CH3:1])[CH2:3][CH2:4][O:5][CH2:6][C@@H:7]1[CH2:11][C@H:10]([S:12][C:13]2[C@H:19]([CH3:20])[C@H:18]3[N:15]([C:16](=[O:24])[C@@H:17]3[C@H:21]([OH:23])[CH3:22])[C:14]=2[C:25]([OH:27])=[O:26])[CH2:9][NH:8]1

Participants

6

Reactant 2

HCID 86744489HCID 86744489, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67929791HCID 67929791, compoundYield 29.1%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 175AcetateSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-{2-(dimethylamino)ethyloxymethyl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.48 g) in a mixture of tetrahydrofuran (60 ml) and 0.3 M acetate buffer (pH 5.8) (60 ml) was stirred at ambient temperature for 6 hours in the presence of 20% palladium hydroxide on carbon (0.5 g) under atmospheric pressure of hydrogen. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to remove the tetrahydrofuran The resulting aqueous solution was washed with ethyl acetate (50 ml×3) and evaporated to remove the organic solvent The residual solution was subjected to a column chromatography on nonionic adsorption resin, "Diaion HP-20" (60 ml) and eluted with a mixture of acetone and water (2:98 V/V). The fractions containing the desired compound were collected and 0.5M aqueous acetic acid (1.5 ml) was added to the solution The solution was lyophilized to give (4R,5S,6S)-3-[(2S,4S)-2-{2-(dimethylamino)ethyloxymethyl}pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid monoacetate (0.14 g).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customto remove the tetrahydrofuran The resulting aqueous solution
  4. washwas washed with ethyl acetate (50 ml×3)
  5. customevaporated
  6. customto remove the organic solvent The residual solution
  7. wash" (60 ml) and eluted with a mixture of acetone and water (2:98 V/V)
  8. additionThe fractions containing the desired compound
  9. customwere collected
  10. addition0.5M aqueous acetic acid (1.5 ml) was added to the solution The solution

Sources & evidence

ORD record
ord-be7bad039ce94dc9b4c30cd30b38bc2c
Source dataset
uspto-grants-1991_01
Patent number
US04983596

Reaction notes

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