Trisodium Phosphate → HCID 86741287, compound

HRID 235763Notes

Reaction equation

HRID 235763 reaction equation
P([O-])([O-])([O-])=O.[Na+:6].[Na+].[Na+].[N:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH2:22][C@H:21]3[N:18]([C:19](=[O:40])[C@H:20]3[C:23]([CH3:39])([O:25]C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)[CH3:24])[C:17]=2[C:41]([O:43]CC2C=CC([N+]([O-])=O)=CC=2)=[O:42])=[CH:11][CH:10]=1.C(=O)(O)[O-].[Na+]>[Pd].O1CCOCC1>[N:9]1[CH:14]=[CH:13][C:12]([S:15][C:16]2[CH2:22][C@H:21]3[N:18]([C:19](=[O:40])[C@H:20]3[C:23]([OH:25])([CH3:39])[CH3:24])[C:17]=2[C:41]([O-:43])=[O:42])=[CH:11][CH:10]=1.[Na+:6]

Participants

6

Reactant 3

HCID 24243Trisodium Phosphate2×HCID 516892Sodium BicarbonateHCID 18606587HCID 18606587, compound

Product 1

HCID 86741287HCID 86741287, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 5% palladium on activated charcoal (50 ml), dioxane (3.5 ml) and 1/30M sodium phosphate buffer solution (pH 7.0, 1.5 ml) was shaken for an hour under hydrogen atmosphere (40 psi) at ambient temperature. To this mixture was added a solution of 4-nitrobenzyl(5R,6R)-3-(4-pyridylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (43 mg) in a mixture of dioxane (3.5 ml) and 1/30M sodium phosphate buffer solution (pH 7.0, 1.5 ml) at 0° C., and the resultant mixture was shaken under hydrogen atmosphere (40 psi) for 100 minutes, during which time the reaction temperature rose to ambient temperature. After addition of 1% aqueous sodium bicarbonate (0.57 ml) at 0° C., the mixture was filtered through cellulose powder. The filter-cake was washed with water (3×10 ml). The combined filtrates were concentrated to half of the original volume. The concentrate was washed with ethyl acetate (3×20 ml) and evaporated in vacuo. The residue was dissolve in water (60 ml) containing sodium chloride (1.75 g) and then chromatographed on nonionic adsorption resin "Diaion HP-20" (Trade Mark, maker: Mitsubishi Chemical Industries Ltd. (1.5×20 cm) eluting with water (100 ml) and a mixture of water and acetone (10:0 to 7:3, 200 ml). The fractions, whose UV spectra showed λmax 302 nm, were collected and lyophilized to give sodium (5R,6R)-3-(4-pyridylthio)-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo[3.2.0]-hept-2-ene-2-carboxylate (13.7 mg) as white powder.

Workup

  1. customrose to ambient temperature
  2. filtrationthe mixture was filtered through cellulose powder
  3. washThe filter-cake was washed with water (3×10 ml)
  4. concentrationThe combined filtrates were concentrated to half of the original volume
  5. washThe concentrate was washed with ethyl acetate (3×20 ml)
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolve in water (60 ml)
  8. additioncontaining sodium chloride (1.75 g)
  9. customchromatographed on nonionic adsorption resin "Diaion HP-20" (Trade Mark, maker
  10. wash(1.5×20 cm) eluting with water (100 ml)
  11. additiona mixture of water and acetone (10:0 to 7:3, 200 ml)
  12. customwere collected

Sources & evidence

ORD record
ord-e732de99871048cf8ea4766238321ce1
Source dataset
uspto-grants-1987_02
Patent number
US04640915

Reaction notes

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