Tetrabutylammonium → 3-Amino-2,2-dimethyl-4-oxoazetidine-1-sulfonic acid

HRID 867650Notes

Reaction equation

HRID 867650 reaction equation
[N:1]([CH:4]1[C:7]([CH3:9])([CH3:8])[N:6]([S:10]([OH:13])(=[O:12])=[O:11])[C:5]1=[O:14])=[N+]=[N-].C([N+](CCCC)(CCCC)CCCC)CCC>CO.[Pd]>[NH2:1][CH:4]1[C:7]([CH3:9])([CH3:8])[N:6]([S:10]([OH:13])(=[O:11])=[O:12])[C:5]1=[O:14]

Participants

5

Reactant 2

HCID 16028TetrabutylammoniumHCID 21289895HCID 21289895, compound

Product 1

HCID 137521213-Amino-2,2-dimethyl-4-oxoazetidine-1-sulfonic acidYield 48.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 0.155 g of (±)-3-azido-4,4-dimethyl-2-oxo-1-azetidinesulfonic acid, tetrabutylammonium in 0.6 ml of methanol is hydrogenated over 10% palladium on charcoal for 20 minutes at 1 atmosphere. The catalyst is filtered off and rinsed with methylene chloride which is combined with the methanol solution. This clear solution is treated with 0.123 ml 97% formic acid. Upon addition of the acid the solution immediately becomes cloudy. After standing for 1 hour at 5° C., the solid is filtered off to yield 0.0664 g of the title compound.

Workup

  1. filtrationThe catalyst is filtered off
  2. washrinsed with methylene chloride which
  3. additionThis clear solution is treated with 0.123 ml 97% formic acid
  4. additionUpon addition of the acid the solution immediately becomes cloudy
  5. filtrationthe solid is filtered off

Sources & evidence

ORD record
ord-fcc3193381834b27849c74cb046e30c9
Source dataset
uspto-grants-1988_10
Patent number
US04775670

Reaction notes

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