(3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]-amino]-4-methyl-1-azetidinesulfonic acid, 8-hydroxyquinolinium salt → (3S-trans)-3-Benzyloxycarbonylamino-4-methylazetidinone

HRID 279766Notes

Reaction equation

HRID 279766 reaction equation
OC1C=CC=C2C=1[NH+]=CC=C2.[O:12]=[C:13]1[C@@H:16]([NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])[C@H:15]([CH3:28])[N:14]1S([O-])(=O)=O>C(#N)C>[C:22]1([CH2:21][O:20][C:18]([NH:17][C@H:16]2[C@H:15]([CH3:28])[NH:14][C:13]2=[O:12])=[O:19])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

3

Reactant 1

HCID 131714652(3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]-amino]-4-methyl-1-azetidinesulfonic acid, 8-hydroxyquinolinium salt

Product 1

HCID 13182463(3S-trans)-3-Benzyloxycarbonylamino-4-methylazetidinoneYield 110%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (3S-trans)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid, 8-hydroxyquinolinium salt (150 mg, 0.326 mmol) in acetonitrile (10 ml) was brought rapidly to reflux by lowering the reaction vessel into a preheated oil bath. The mixture was refluxed for a total of 9 minutes during which time a precipitate formed. After cooling to room temperature, the mixture was filtered and solvent was removed from the filtrate in vacuo. The resulting residue was partially dissolved in a small amount of acetonitrile and the addition of ethyl acetate caused further precipitation. After decanting the supernatant, the procedure was repeated on the solid. The remaining solid was triturated with ethyl acetate and decanted. The supernatants were filtered through Celite, combined, and solvent was removed under reduced pressure yielding an oil (84 mg). The crude product was purified by column chromatography on silica gel (2 g, Mallinckrodt SilicAR CC-4). Elution with 5% acetonitrile: 95% ethyl acetate afforded the desired product (56 mg).

Workup

  1. temperatureto reflux
  2. temperatureThe mixture was refluxed for a total of 9 minutes during which time a precipitate
  3. customformed
  4. filtrationthe mixture was filtered
  5. customsolvent was removed from the filtrate in vacuo
  6. dissolutionThe resulting residue was partially dissolved in a small amount of acetonitrile
  7. additionthe addition of ethyl acetate caused further precipitation
  8. customAfter decanting the supernatant
  9. customThe remaining solid was triturated with ethyl acetate
  10. customdecanted
  11. filtrationThe supernatants were filtered through Celite
  12. customsolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-7429aee174944f1cb77189173239b4ef
Source dataset
uspto-grants-1986_05
Patent number
US04587051

Reaction notes

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