Reacción #64405

Ecuación de reacción

methylamine

ethanol

N-Boc-4-cyanophenylalanine

pentafluorophenol

4-methylmorpholine

→

title compound

Rendimiento 92.0%

N-Boc-4-cyanophenylalanine-N-methylamide

Rendimiento 92.0%

Disolventes

CH2Cl2

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITthe reaction mixture left
2. 2
   workup.STIRRINGto stir at room temperature for 16 hours
3. 3
   OtroThe solvent was removed under pressure
4. 4
   workup.DISSOLUTIONthe residue dissolved in CH2Cl2 (50 ml)
5. 5
   Lavadowashed with saturated sodium bicarbonate (2×50 ml), 1M citric acid (2×50 ml) and brine (50 ml)
6. 6
   SecadoThe CH2Cl2 layer was dried over MgSO4
7. 7
   Otrothe solvent removed under pressure

Procedimiento

A solution of N-Boc-4-cyanophenylalanine (1.92 g, 6.6 mmol) and pentafluorophenol (2.43 g, 13.2 mmol) in CH2Cl2 (30 ml) at 0° C. was treated with 4-methylmorpholine (0.74 g, 7.3 mmol). After stirring the reaction mixture for 3 hours, 8M methylamine in ethanol (15 ml, 19.8 mmol) was added and the reaction mixture left to stir at room temperature for 16 hours. The solvent was removed under pressure, the residue dissolved in CH2Cl2 (50 ml) and washed with saturated sodium bicarbonate (2×50 ml), 1M citric acid (2×50 ml) and brine (50 ml). The CH2Cl2 layer was dried over MgSO4 and the solvent removed under pressure to yield the title compound as a white solid (1.84 g, 92%).

Fuente