Tetrahydrofuran → HCID 13344800, compound

HRID 225160Notes

Reaction equation

HRID 225160 reaction equation
[CH:1](=[C:3]1[C:9](=[O:10])[N:8]2[CH:4]1[CH2:5][C:6]([S:24][CH2:25][CH2:26][NH:27]C(OCC1C=CC([N+]([O-])=O)=CC=1)=O)=[C:7]2[C:11]([O:13]CC1C=CC([N+]([O-])=O)=CC=1)=[O:12])[CH3:2].C1COCC1>O=[Pt]=O.CCO>[CH2:1]([CH:3]1[C:9](=[O:10])[N:8]2[CH:4]1[CH2:5][C:6]([S:24][CH2:25][CH2:26][NH2:27])=[C:7]2[C:11]([OH:13])=[O:12])[CH3:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 54376555HCID 54376555, compound

Product 1

HCID 13344800HCID 13344800, compound

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A mixture of p-nitrobenzyl 6-ethylidene-3-[2-(p-nitrobenzyloxycarbonylamino)ethylthio]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (37 mg), PtO2 (40 mg), THF (4 ml) and EtOH (2 ml) is hydrogenated at 50 psi and 25° C., for 2.5 hrs. The catalyst is filtered off and washed thoroughly with 0.1 M pH 7 phosphate buffer (5 ml). The combined filtrate and washings are concentrated in vacuo to remove most of the organic solvents. The aqueous residue is chromatographed on a column of Dowex-50×4 (Na Form) ion-exchange resin; the product being eluted with deionized H2O. The appropriate fractions are combined and lyophilized to afford 6-ethyl-3-(2-aminoethyl)thio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid.

Workup

  1. filtrationThe catalyst is filtered off
  2. washwashed thoroughly with 0.1 M pH 7 phosphate buffer (5 ml)
  3. concentrationThe combined filtrate and washings are concentrated in vacuo
  4. customto remove most of the organic solvents
  5. customThe aqueous residue is chromatographed on a column of Dowex-50×4 (Na Form) ion-exchange resin
  6. washthe product being eluted with deionized H2O

Sources & evidence

ORD record
ord-1c899152476b4a08b44359add0fbb51b
Source dataset
uspto-grants-1980_11
Patent number
US04235922

Reaction notes

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