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

HRID 279767Notes

Reaction equation

HRID 279767 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(O)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 83.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(3S-trans)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-1-azetidinesulfonic acid, 8-hydroxyquinolinium salt (230 mg, 0.5 mmol; see Method IA) was dissolved in absolute ethanol (10 ml) and refluxed for 4 hours. Ethanol was removed in vacuo yielding a residue which was triturated with ethyl acetate (5×10 ml). From the combined extract, solvent was removed in vacuo affording a residue which was chromatographed on silica gel (Mallinckrodt CC-7). Elution with ethyl acetate yielded (3S-trans)-3-[[(phenylmethoxy)carbonyl]amino]-4-methyl-2-azetidinone (98 mg).

Workup

  1. temperaturerefluxed for 4 hours
  2. customEthanol was removed in vacuo
  3. customyielding a residue which
  4. customwas triturated with ethyl acetate (5×10 ml)
  5. extractionFrom the combined extract
  6. customsolvent was removed in vacuo
  7. customaffording a residue which
  8. customwas chromatographed on silica gel (Mallinckrodt CC-7)
  9. washElution with ethyl acetate

Sources & evidence

ORD record
ord-a8310bacfb5c4091a730a3af39e3b4a2
Source dataset
uspto-grants-1986_05
Patent number
US04587051

Reaction notes

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