HCID 23329199, compound → HCID 13344800, compound

HRID 225159Notes

Reaction equation

HRID 225159 reaction equation
[CH2:1]([CH:3]1[C:9](=[O:10])[N:8]2[CH:4]1[CH2:5][C:6]([S:21][CH2:22][CH2:23][NH:24]C(OCC1C=CC=CC=1)=O)=[C:7]2[C:11]([O:13]CC1C=CC=CC=1)=[O:12])[CH3:2]>[Pd].O1CCOCC1.O>[CH2:1]([CH:3]1[C:9](=[O:10])[N:8]2[CH:4]1[CH2:5][C:6]([S:21][CH2:22][CH2:23][NH2:24])=[C:7]2[C:11]([OH:13])=[O:12])[CH3:2]

Participants

4

Reactant 1

HCID 23329199HCID 23329199, compound

Product 1

HCID 13344800HCID 13344800, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of benzyl 6-ethyl-3-(2-benzyloxycarbonyl aminoethyl)thio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (10 mg) and 10% Pd/C (20 mg) in 1:1 dioxane-H2O (4 ml) is hydrogenated at 40 psi for 1 hr. The mixture is filtered to remove the catalyst which is washed with more H2O (4 ml). The combined filtrate and washings are concentrated in vacuo to 2 ml and loaded onto a column of 200-400 mesh Dowex-50×4 (Na form) ion-exchange resin. The column is eluted with deionized H2O. The appropriate fractions are pooled and lyophilized to provide 6-ethyl-3-(2-aminoethyl)thio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid.

Workup

  1. filtrationThe mixture is filtered
  2. customto remove the catalyst which
  3. washis washed with more H2O (4 ml)
  4. concentrationThe combined filtrate and washings are concentrated in vacuo to 2 ml
  5. washThe column is eluted with deionized H2O

Sources & evidence

ORD record
ord-235976da01b644a889f7f044f0ba6113
Source dataset
uspto-grants-1980_11
Patent number
US04235922

Reaction notes

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