Reacción #2175513

Ecuación de reacción

amide

2-benzyloxycarbonylamino-4-carbamoyl-butyric acid ethyl ester

t-butyl nitrite

→

( 3 )

Rendimiento 64.7%

2-benzyloxycarbonylamino-pentanedioic acid 1-ethyl ester

Rendimiento 64.7%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux under nitrogen
2. 2
   TemperaturaAfter cooling
3. 3
   Otrothe solvent was removed in a rotary evaporator
4. 4
   workup.STIRRINGethyl acetate (500 ml) and the biphasic mixture was stirred well while solid sodium bicarbonate
5. 5
   workup.ADDITIONwas slowly added to pH=7.5
6. 6
   OtroPhases were separated
7. 7
   Lavadothe organic phase was washed with 10% sodium bicarbonate (200 ml)
8. 8
   LavadoThe combined aqueous extracts were washed with ethyl acetate (300 ml)
9. 9
   Extracciónextracted with ethyl acetate (2×300 ml)
10. 10
    LavadoThe combined extracts were washed with water (150 ml)
11. 11
    Secadodried over sodium sulfate
12. 12
    Otrothe residue was dried in a vacuum oven (50° C.)

Procedimiento

A suspension of the amide (2) (38 g, 0.1233 mol) in anhydrous acetonitrile (400 ml) was stirred at reflux under nitrogen and t-butyl nitrite (35 ml, 3.17 equiv.) was added quickly. The reflux was continued for 2 hrs. After cooling, the solvent was removed in a rotary evaporator. The residue was taken in water (250 ml) and ethyl acetate (500 ml) and the biphasic mixture was stirred well while solid sodium bicarbonate was slowly added to pH=7.5. Phases were separated and the organic phase was washed with 10% sodium bicarbonate (200 ml). The combined aqueous extracts were washed with ethyl acetate (300 ml), made acidic with 6N hydrochloric acid and extracted with ethyl acetate (2×300 ml). The combined extracts were washed with water (150 ml), dried over sodium sulfate, stripped and the residue was dried in a vacuum oven (50° C.) to produce (3) (24.6 g, 64.7%).

Fuente