p-Toluenesulfonic acid → Methyl (2R,3R)-3-amino-4-oxoazetidine-2-carboxylate

HRID 127895Notes

Reaction equation

HRID 127895 reaction equation
[N:1]([C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[C:9]([O:11][CH3:12])=[O:10])=[N+]=[N-].C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C.[Pd]>[NH2:1][C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 13566680Methyl (2R,3R)-3-azido-4-oxoazetidine-2-carboxylate

Product 1

HCID 14230520Methyl (2R,3R)-3-amino-4-oxoazetidine-2-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of methyl cis-3-azido-4-oxoazetidine-2-carboxylate (8.5 g, 50 mmol) and an equivalent of p-toluenesulfonic acid in 200 ml of ethanol is hydrogenated for 3 hours over 1 g of 10% Pd on carbon at 40 psi. The solution is filtered and the filtrate is evaporated to title product or the tosylate salt which can be converted to the free base by standard methods.

Workup

  1. filtrationThe solution is filtered
  2. customthe filtrate is evaporated to title product

Sources & evidence

ORD record
ord-8c41c06effe04787b56a53024de49fa4
Source dataset
uspto-grants-1981_03
Patent number
US04257947

Reaction notes

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