Réaction #64405

Équation de réaction

methylamine

ethanol

N-Boc-4-cyanophenylalanine

pentafluorophenol

4-methylmorpholine

→

title compound

Rendement 92.0%

N-Boc-4-cyanophenylalanine-N-methylamide

Rendement 92.0%

Solvants

CH2Cl2

Conditions de réaction

Traitement

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

Mode opératoire

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%).

Source