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