Sulfuric acid magnesium salt (1:1) → N-(cis-4-oxo-3-phenoxyacetylamino-2-azetidinylmethyl)iminoacetic acid benzyl ester

HRID 2050399Notes

Reaction equation

HRID 2050399 reaction equation
[N:1]([CH2:4][C@H:5]1[C@@H:8]([NH:9][C:10](=[O:19])[CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7](=[O:20])[NH:6]1)=[N+]=[N-].S([O-])([O-])(=O)=O.[Mg+2].[C:27]([O:31][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)(=[O:30])[CH:28]=O>[Pd].C(O)C.C(Cl)Cl>[CH2:32]([O:31][C:27](=[O:30])[CH:28]=[N:1][CH2:4][C@H:5]1[C@@H:8]([NH:9][C:10](=[O:19])[CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:7](=[O:20])[NH:6]1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

7

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 11008258Benzyl glyoxylateHCID 86734330HCID 86734330, compound

Product 1

HCID 70593479N-(cis-4-oxo-3-phenoxyacetylamino-2-azetidinylmethyl)iminoacetic acid benzyl ester

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 0.499 g (1.81 mmole) of cis-2-azidomethyl-4-oxo-3-phenoxyacetylaminoazetidine and 0.189 g of 10% palladium on carbon in 25 ml of absolute ethanol was hydrogenated at atmospheric pressure and at 40° for 1 hour. The solution was filtered through celite and the solvent was removed in vacuo to afford a colorless gum which was dissolved in 15 ml of methylene dichloride. Anhydrous magnesium sulfate was added followed by addition of a solution of 0.314 g (1.91 mmole) of benzyl glyoxalate in 10 ml of methylene dichloride. The reaction mixture was stirred at room temperature under argon for 2.5 hours then was allowed to stand at 0° overnight. After filtering the reaction mixture, the solvents were removed in vacuo to give a semi-crystalline residue which was recrystallized from ethyl acetate-hexane to give N-(cis-4-oxo-3-phenoxyacetylamino-2-azetidinylmethyl)iminoacetic acid benzyl ester as a colorless solid.

Workup

  1. filtrationThe solution was filtered through celite
  2. customthe solvent was removed in vacuo
  3. customto afford a colorless gum which
  4. waitto stand at 0° overnight
  5. filtrationAfter filtering the reaction mixture
  6. customthe solvents were removed in vacuo
  7. customto give a semi-crystalline residue which
  8. customwas recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-a74443beedf044e385da71aebdf6267a
Source dataset
uspto-grants-1980_04
Patent number
US04200572

Reaction notes

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