Reaction #1135863

Reaction equation

trans-3-{N′-(6-carboxymethoxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl}-(R)-piperidin-1-carboxylic acid tert-butyl ester

trifluoroacetic acid

→

titled compound

Yield 50.0%

trans-{7-oxo-2-[N′—((R)-piperidin-3-carbonyl)-hydrazinocarbonyl]-1,6-diaza-bicyclo[3.2.1]-oct-6-yloxy}-acetic acid

Yield 50.0%

Solvents

dichloromethane

Conditions

Workup

1. 1
   workup.STIRRINGThe reaction mixture was stirred for about 1 hour at −10° C.
2. 2
   Otherthe solvents were evaporated under vacuum
3. 3
   Otherto provide a residue
4. 4
   OtherThe residue was triturated successively with diethyl ether (25 ml) and acetonitrile (25 ml) and solvents
5. 5
   Otherwere decanted
6. 6
   Otherto provide solid
7. 7
   Otherthat was dried under vacuum

Procedure

To a clear solution of trans-3-{N′-(6-carboxymethoxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl}-(R)-piperidin-1-carboxylic acid tert-butyl ester (150 mg, 0.32 mmol) in dichloromethane (2 ml) was added trifluoroacetic acid under stirring at −10° C. The reaction mixture was stirred for about 1 hour at −10° C. and the solvents were evaporated under vacuum to provide a residue. The residue was triturated successively with diethyl ether (25 ml) and acetonitrile (25 ml) and solvents were decanted to provide solid that was dried under vacuum to provide 59 mg of titled compound in 50% yield.

Source