Reaction #1135862

Reaction equation

ethyl acetate

potassium hydrogen sulfate

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

lithium hydroxide

→

tilted intermediate

Yield 28.4%

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

Yield 28.4%

Solvents

tetrahydrofuran

water

Conditions

Workup

1. 1
   OtherLayers were separated
2. 2
   Extractionextracted with ethyl acetate (3×25 ml)
3. 3
   DryingThe Organic layer was dried over sodium sulfate
4. 4
   Otherevaporated to dryness under vacuum

Procedure

To a clear solution of trans-3-{N′-(6-ethoxycarbonylmethoxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)-hydrazinocarbonyl}-(R)-piperidin-1-carboxylic acid tert-butyl ester (600 mg, 1.20 mmol) in tetrahydrofuran (32 ml) and water (12 ml) was added lithium hydroxide (43.2 mg, 1.8 mmol) at 0° C. The reaction mixture was stirred for 3 hours and was neutralized to pH 6 by addition of aqueous 1 N potassium hydrogen sulfate. It was exacted with ethyl acetate (3×25 ml). Layers were separated and aqueous layer was acidified with 1 N potassium hydrogen sulfate to pH 1 and extracted with ethyl acetate (3×25 ml). The Organic layer was dried over sodium sulfate and evaporated to dryness under vacuum to provide 160 mg of tilted intermediate as a solid in 27% yield.

Source