tetrabutylammonium (S)-3-(((benzyloxy)carbonyl)amino)-2-oxoazetidine-1-sulfonate → benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

HRID 279770Notes

Reaction equation

HRID 279770 reaction equation
C([N+](CCCC)(CCCC)CCCC)CCC.[O:18]=[C:19]1[C@@H:22]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:21][N:20]1S([O-])(=O)=O.C1(C)C=CC(S([O-])(=O)=O)=CC=1.OC1C=CC=C2C=1[NH+]=CC=C2>C(#N)C>[C:28]1([CH2:27][O:26][C:24]([NH:23][C@H:22]2[CH2:21][NH:20][C:19]2=[O:18])=[O:25])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 13575530tetrabutylammonium (S)-3-(((benzyloxy)carbonyl)amino)-2-oxoazetidine-1-sulfonateHCID 233225528-Hydroxyquinolinium p-toluenesulfonate

Product 1

HCID 12834624benzyl N-[(3S)-2-oxoazetidin-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3S)-2-oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt in acetonitrile was added 8-hydroxyquinolinium p-toluenesulfonate. The mixture was refluxed, yielding the title compound as verified by thin layer chromatography (Merck silica gel 60F, ethyl acetate).

Workup

  1. temperatureThe mixture was refluxed

Sources & evidence

ORD record
ord-ab3570933fde440d99531e40132d99ab
Source dataset
uspto-grants-1986_05
Patent number
US04587051

Reaction notes

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