Potassium Phosphate, Dibasic → HCID 178434146, compound

HRID 235777Notes

Reaction equation

HRID 235777 reaction equation
[CH3:1][C:2]([C@@H:18]1[C:24](=[O:25])[N:23]2[C@@H:19]1[CH2:20][C:21]([S:39][C:40]1[NH:44][C:43]([CH3:45])=[N:42][N:41]=1)=[C:22]2[C:26]([O:28]CC1C=CC([N+]([O-])=O)=CC=1)=[O:27])([O:4]C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)[CH3:3].O1CCOCC1.P([O-])([O-])(O)=O.[K+:57].[K+]>[Pd].C(O)C>[OH:4][C:2]([C@@H:18]1[C:24](=[O:25])[N:23]2[C@@H:19]1[CH2:20][C:21]([S:39][C:40]1[NH:44][C:43]([CH3:45])=[N:42][N:41]=1)=[C:22]2[C:26]([O-:28])=[O:27])([CH3:3])[CH3:1].[K+:57]

Participants

6

Reactant 3

HCID 24450Potassium Phosphate, DibasicHCID 312751,4-DioxaneHCID 178434145HCID 178434145, compound

Product 1

HCID 178434146HCID 178434146, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-nitrobenzyl (5R, 6R)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-3-(5-methyl-4H-1,2,4-triazol-3-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (50 mg) and 5% palladium on activated carbon (50 mg) in 0.048M aqueous dipotassium hydrogen phosphate (4.85 ml), ethanol (0.5 ml), and dioxane (6.0 ml) was shaken for 2 hours under a hydrogen atmosphere (40 psi) at ambient temperature. After the catalyst was filtered off, the filtrate was concentrated to half of the original volume. The aqueous concentrate was washed three times with diethyl ether and evaporated in vacuo. The residue was chromatographed on nonionic adsorption resin "Diaion CHP-20P", eluting with water (100 ml) and 5% aqueous isopropyl alcohol (100 ml). The fractions, whose UV spectra showed λmax 292 nm, were combined and lyophilized to give potassium (5R, 6R)-6-(1-hydroxy-1-methylethyl)-3-(5-methyl- 4H-1,2,4-triazol-3-ylthio)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (13.2 mg) as a yellow powder.

Workup

  1. filtrationAfter the catalyst was filtered off
  2. concentrationthe filtrate was concentrated to half of the original volume
  3. concentrationThe aqueous concentrate
  4. washwas washed three times with diethyl ether
  5. customevaporated in vacuo
  6. customThe residue was chromatographed on nonionic adsorption resin "Diaion CHP-20P"
  7. washeluting with water (100 ml) and 5% aqueous isopropyl alcohol (100 ml)

Sources & evidence

ORD record
ord-8f443b43326b42fda5250cd0bcd5a0d2
Source dataset
uspto-grants-1987_02
Patent number
US04640915

Reaction notes

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