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

HRID 616158Notes

Reaction equation

HRID 616158 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-272c3405d8f4491695f8ea537b832498
Source dataset
uspto-grants-1978_02
Patent number
US04072674

Reaction notes

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