Phosphate → HCID 54369112, compound

HRID 620800Notes

Reaction equation

HRID 620800 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]([CH3:52])[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:49]([NH2:51])=[O:50])[CH2:27]1)=[C:8]2[C:12]([O:14]CC1C=CC([N+]([O-])=O)=CC=1)=[O:13])[CH3:3].P([O-])([O-])([O-])=O.[H][H]>[OH-].[OH-].[Pd+2].O1CCCC1>[OH:1][C@@H:2]([C@H:4]1[C:10](=[O:11])[N:9]2[C@@H:5]1[C@@H:6]([CH3:52])[C:7]([S:25][C@@H:26]1[CH2:30][NH:29][C@H:28]([CH2:44][O:45][CH2:46][CH2:47][NH:48][C:49]([NH2:51])=[O:50])[CH2:27]1)=[C:8]2[C:12]([OH:14])=[O:13])[CH3:3]

Participants

6

Reactant 3

HCID 1061PhosphateHCID 53656297HCID 53656297, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54369112HCID 54369112, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-{(2-ureidoethyl)oxylmethyl}pyrrolidin-4-yl]thio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.75 g), tetrahydrofuran (40 ml), 0.1M phosphate buffer (pH 6.5) (20 ml) and 20% palladium hydroxide on carbon (0.20 g) was stirred at ambient temperature for 5 hours under atmospheric pressure of hydrogen. 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 "Diaion HP-20" (40 ml) eluting with a mixture of acetone and water (5:95 V/V), and lyophilized to give (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(2S,4S)-2-{(2-ureidoethyl)oxymethyl}pyrrolidin-4-yl]thio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.20 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. wash" (40 ml) eluting with a mixture of acetone and water (5:95 V/V)

Sources & evidence

ORD record
ord-f6f48caac41845808469e8e26b152d29
Source dataset
uspto-grants-1989_04
Patent number
US04822787

Reaction notes

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