Reacción #543539

Ecuación de reacción

[3-(2-carboxyethyl)]-3-nitropentane-1,5-dicarboxylic acid

cesium carbonate

benzylbromide

→

benzyl ester

Rendimiento 82.2%

1,5-Bis(benzyloxycarbonyl)-3-[2-(benzyloxycarbony)ethyl]-3-nitro pentane

Rendimiento 82.2%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónInorganic salts were filtered
2. 2
   Lavadothe salts washed with acetonitrile
3. 3
   Otroevaporated
4. 4
   Otroto obtain an oil
5. 5
   OtroPurification by chromatography over silica gel (hexane: ethyl acetate, 7:3)

Procedimiento

To a mixture of [3-(2-carboxyethyl)]-3-nitropentane-1,5-dicarboxylic acid (2.8 g, 0.01 mole) (prepared as described by James K. Young et al., Macromolecules, 1994, 27, 3464-34-71) and cesium carbonate (3.25 g, 0.025 mol) in acetonitrile (20.0 mL) was added benzylbromide (8.55 g, 6.0 mL, 0.05 mole) and the mixture stirred at RT for 24 h. Inorganic salts were filtered and the salts washed with acetonitrile. The filtrate and the washings were combined and evaporated to obtain an oil. Purification by chromatography over silica gel (hexane: ethyl acetate, 7:3) afforded the benzyl ester (40) as colorless viscous oil (4.5 g, yield: 82%). Mass Spectrum (M+H)hu +=548.

Fuente