p-Toluenesulfonic acid monohydrate → (3S,4S)-3-amino-4-azido-2-oxoazetidine

HRID 978838Notes

Reaction equation

HRID 978838 reaction equation
[N:1]([C@@H:4]1[NH:7][C:6](=[O:8])[C@H:5]1[NH:9]C(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[N+:2]=[N-:3].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CC(C)=O>[NH2:9][C@H:5]1[C@H:4]([N:1]=[N+:2]=[N-:3])[NH:7][C:6]1=[O:8]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 53771026(3S,4S)-4-azido-3-tritylamino-2-azetidinone

Product 1

HCID 54269820(3S,4S)-3-amino-4-azido-2-oxoazetidine

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 1.3 g of (3S,4S)-4-azido-3-tritylamino-2-oxoazetidine in 15 ml of acetone is added 0.736 g of p-toluenesulfonic acid monohydrate. The mixture is treated in a same manner to Reference Example 45B to give 0.886 g of tosyl salt of (3S,4S)-3-amino-4-azido-2-oxoazetidine.

Workup

  1. additionThe mixture is treated in a same manner to Reference Example 45B

Sources & evidence

ORD record
ord-a83351d8636d426aac89df724d54814a
Source dataset
uspto-grants-1987_05
Patent number
US04665067

Reaction notes

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