Reacción #486707

Ecuación de reacción

(4S)-1-(tert-butyloxycarbonyl)-4-(p-nitrobenzoyloxy)-L-proline tert-butyl ester

sodium hydroxide

→

title compound

Rendimiento 82.5%

(4S)-1-(tert-Butyloxycarbonyl)-4-hydroxy-L-Proline tert-Butyl Ester

Rendimiento 82.5%

Disolventes

ethanol

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Lavadowashed with water (2×), saturated brine solution
2. 2
   Secadodried (Na2SO4)
3. 3
   Otroevaporated
4. 4
   Lavadoeluting with 5% acetone/dichloromethane

Procedimiento

A solution of (4S)-1-(tert-butyloxycarbonyl)-4-(p-nitrobenzoyloxy)-L-proline tert-butyl ester (575 mg, 1.32 mmol) in ethanol (13 mL) was treated with 0.4N sodium hydroxide (4.3 mL, 1.72 mmol) for 18 hours at room temperature. The solution was neutralized with several drops of glacial acetic acid, diluted with ethyl acetate (100 mL), washed with water (2×), saturated brine solution, dried (Na2SO4), and evaporated. The residue was subjected to flash silica gel chromatography eluting with 5% acetone/dichloromethane. The title compound (313 mg) was obtained contaminated with some p-nitrobenzoic acid and used without further purification in the next step.

Fuente