HCID 131714653, compound → benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate
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])[CH2:15][N:14]1S([O-])(=O)=O>C(#N)C>[C:22]1([CH2:21][O:20][C:18]([NH:17][C@H:16]2[CH2:15][NH:14][C:13]2=[O:12])=[O:19])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
(3S)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, 8-hydroxyquinolinium salt (150 mg, 0.337 mmol) was added to acetonitrile (10 ml) and rapidly heated to reflux in a preheated oil bath. After refluxing for a total of 18 minutes, the mixture was cooled to room temperature, filtered through Celite, and solvent was removed in vacuo. The residue was extracted with an acetonitrile-ethyl acetate mixture and the extract chromatographed on a silica gel column (Mallinckrodt SilicAR CC-7). The desired product (31 mg) was eluted with a 5% acetonitrile:95% ethyl acetate mixture.