Trisodium Phosphate → HCID 86740288, compound

HRID 1719335Notes

Reaction equation

HRID 1719335 reaction equation
P([O-])([O-])([O-])=O.[Na+:6].[Na+].[Na+].[C:9]([NH:12][CH2:13][CH2:14][S:15][C:16]1[CH2:22][C@H:21]2[N:18]([C:19](=[O:40])[C@H:20]2[C:23]([CH3:39])([O:25]C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[CH3:24])[C:17]=1[C:41]([O:43]CC1C=CC([N+]([O-])=O)=CC=1)=[O:42])(=[O:11])[CH3:10].C(=O)(O)[O-].[Na+]>[Pd].O1CCOCC1>[C:9]([NH:12][CH2:13][CH2:14][S:15][C:16]1[CH2:22][C@H:21]2[N:18]([C:19](=[O:40])[C@H:20]2[C:23]([OH:25])([CH3:24])[CH3:39])[C:17]=1[C:41]([O-:43])=[O:42])(=[O:11])[CH3:10].[Na+:6]

Participants

6

Reactant 3

HCID 24243Trisodium Phosphate2×HCID 516892Sodium BicarbonateHCID 86740287HCID 86740287, compound

Product 1

HCID 86740288HCID 86740288, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 5% palladium on activated carbon (175 mg), dioxane (12.5 ml) and 1/30M sodium phosphate buffer (pH 7.0, 5.5 ml) was shaken for an hour under a hydrogen atmosphere (40 psi) at ambient temperature. A solution of 4-nitrobenzyl (5R,6R)-3-(2-acetamidoethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (175 mg) in a mixture of dioxane (12 ml) and 1/30M sodium phosphate buffer (pH7.0, 5 ml) was added to the mixture at 0° C. and the resulting mixture was shaken under a hydrogen atmosphere (40 psi) for an hour, during which time the reaction temperature rose to ambient temperature. 1% Aqueous solution of sodium bicarbonate (2.29 ml) was added therein at 0° C. and the mixture was filtered through cellulose powder. The filter-cake was washed with water (3×20 ml). The combined filtrates were concentrated to a half volume, washed with ethyl acetate (3×50 ml), and evaporated in vacuo. The residue was dissolved in water (220 ml) containing sodium chloride (6.6 g) and chromatographed on Diaion non-ionic adsorption resin, HP-20 AG (trade mark, made by Mitsubishi Chemical Industries) (150-300μ, φ2.2×36 cm) eluting with water (360 ml) and a mixture of water and acetone (10:0 to 7:3, 600 ml). The fractions, whose UV spectra showed λmax 300 nm, were combined and lyophilized to give sodium (5R,6R)-3-(2-acetamidoethylthio)-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (46.5 mg) as white powder.

Workup

  1. additionwas added to the mixture at 0° C.
  2. stirringthe resulting mixture was shaken under a hydrogen atmosphere (40 psi) for an hour
  3. customrose to ambient temperature
  4. filtrationat 0° C. and the mixture was filtered through cellulose powder
  5. washThe filter-cake was washed with water (3×20 ml)
  6. concentrationThe combined filtrates were concentrated to a half volume
  7. washwashed with ethyl acetate (3×50 ml)
  8. customevaporated in vacuo
  9. dissolutionThe residue was dissolved in water (220 ml)
  10. additioncontaining sodium chloride (6.6 g)
  11. customchromatographed on Diaion non-ionic adsorption resin, HP-20 AG (trade mark, made by Mitsubishi Chemical Industries) (150-300μ, φ2.2×36 cm)
  12. washeluting with water (360 ml)
  13. additiona mixture of water and acetone (10:0 to 7:3, 600 ml)

Sources & evidence

ORD record
ord-669961c1933242efa26b593ed7ee40cd
Source dataset
uspto-grants-1985_09
Patent number
US04539152

Reaction notes

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