Sodium Bicarbonate → sodium (5R,6S)-3-(2-acetamido-ethylthio)-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

HRID 851424Notes

Reaction equation

HRID 851424 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:32])[C@@H:12]2[C:15]([CH3:31])([O:17]C(OCC2C=CC([N+]([O-])=O)=CC=2)=O)[CH3:16])[C:9]=1[C:33]([O:35]CC1C=CC([N+]([O-])=O)=CC=1)=[O:34])(=[O:3])[CH3:2].C(=O)([O-])O.[Na+:50]>O.O1CCOCC1.[Pd]>[C:1]([NH:4][CH2:5][CH2:6][S:7][C:8]1[CH2:14][C@H:13]2[N:10]([C:11](=[O:32])[C@@H:12]2[C:15]([OH:17])([CH3:16])[CH3:31])[C:9]=1[C:33]([O-:35])=[O:34])(=[O:3])[CH3:2].[Na+:50]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 228231944-nitrobenzyl (5R,6S)-3-(2-acetamidoethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Product 1

HCID 23698098sodium (5R,6S)-3-(2-acetamido-ethylthio)-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A mixture of 5% palladium-charcoal (40.0 mg), water (0.96 ml) and dioxane (2.24 ml) was shaken for 30 minutes under hydrogen atmosphere (40 psi) at ambient temperature. The mixture was added to a solution of 4-nitrobenzyl (5R,6S)-3-(2-acetamidoethylthio)-6-[1-methyl-1-(4-nitrobenzyloxycarbonyloxy)ethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (40.0 mg) in a mixture of water (0.24 ml) and dioxane (0.56 ml), and shaken for 2 hours under hydrogen atmosphere (40 psi) at ambient temperature. The resulting mixture was added with 1% aqueous sodium hydrogen carbonate (0.522 ml) at 0° C. and filtered by using diatomaceous earth. The filtered cake was washed with water (3×5 ml) and the combined filtrates were concentrated, washed with ethyl acetate (3×20 ml) and evaporated in vacuo. The residue was dissolved in water (25 ml) containing sodium chloride (0.7 g) and chromatographed on a non ionic adsorption resin HP-20 (trademark, made by Mitsubishi Chemical Industries) (1.0×20 cm) eluting with a mixture of water and acetone (100:0 to 7:3, 200 ml). The fractions containing the product were combined and lyophilized to give sodium (5R,6S)-3-(2-acetamido-ethylthio)-6-(1-hydroxy-1-methylethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (6.9 mg) as a white solid.

Workup

  1. stirringshaken for 2 hours under hydrogen atmosphere (40 psi) at ambient temperature
  2. filtrationfiltered
  3. washThe filtered cake was washed with water (3×5 ml)
  4. concentrationthe combined filtrates were concentrated
  5. washwashed with ethyl acetate (3×20 ml)
  6. customevaporated in vacuo
  7. dissolutionThe residue was dissolved in water (25 ml)
  8. additioncontaining sodium chloride (0.7 g)
  9. customchromatographed on a non ionic adsorption resin
  10. wash(trademark, made by Mitsubishi Chemical Industries) (1.0×20 cm) eluting with a mixture of water and acetone (100:0 to 7:3, 200 ml)
  11. additionThe fractions containing the product

Sources & evidence

ORD record
ord-f22cebba048f4a078116b948ba37cdd5
Source dataset
uspto-grants-1983_05
Patent number
US04383945

Reaction notes

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