HCID 12961570, compound → HCID 14782602, compound

HRID 1156732Notes

Reaction equation

HRID 1156732 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([S:7][C:8]2[CH2:14][CH:13]3[N:10]([C:11](=[O:17])[CH:12]3[CH2:15][CH3:16])[C:9]=2[C:18]([O:20]CC2C=CC([N+]([O-])=O)=CC=2)=[O:19])=[CH:3][CH:2]=1.[H][H]>O1CCOCC1.P([O-])([O-])([O-])=O.[Pt]=O>[N:1]1[CH:6]=[CH:5][C:4]([S:7][C:8]2[CH2:14][CH:13]3[N:10]([C:11](=[O:17])[CH:12]3[CH2:15][CH3:16])[C:9]=2[C:18]([OH:20])=[O:19])=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 12961570HCID 12961570, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14782602HCID 14782602, compoundYield 56.8%

Reagents, catalysts & solvents 3

HCID 82844Platinum oxide (PtO)CatalystHCID 1061PhosphateSolventHCID 312751,4-DioxaneSolvent

Procedure

54 mg of p-nitrobenzyl 3-(4-pyridylthio)-6-ethyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate obtained in Example 17 was dissolved in a mixture of 2 ml of dioxane and 2 ml of a 0.1 M phosphate buffer (pH 7.0). Then, 54 mg of platinum oxide was added, and the reaction was performed at room temperature for 4 hours in a Paar reducing apparatus (hydrogen pressure 4 kg/cm2). The catalyst was removed by filtration. The filtrate and the wash liquid were combined and concentrated under reduced pressure to about 2/3 of the original amount. To the resulting solution was added 2.5 g of sodium chloride, and further water was added to make the total amount 50 ml. The solution was charged on a column of Diaion HP-20AG (1.1×20 cm), and eluted with 300 ml in total of an aqueous solution of acetone having a concentration gradually varying from 0 to 30% by a concentration gradient method. The eluate was fractionated into 5 g fractions. The fractions were screened by high-velocity liquid chromatography, and fractions having an ultraviolet absorption at λmax 303 nm were collected, and lyophilized to afford 20.7 mg (yield 56.8%) of the captioned product.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationconcentrated under reduced pressure to about 2/3 of the original amount
  3. additionTo the resulting solution was added 2.5 g of sodium chloride, and further water
  4. additionwas added
  5. additionThe solution was charged on a column of Diaion HP-20AG (1.1×20 cm)
  6. washeluted with 300 ml in total of an aqueous solution of acetone having
  7. concentrationa concentration
  8. customan ultraviolet absorption at λmax 303 nm
  9. customwere collected

Sources & evidence

ORD record
ord-fe45e947556d49759409ee9f8efb33f3
Source dataset
uspto-grants-1982_06
Patent number
US04337199

Reaction notes

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