Reaction #64405

Reaction equation

methylamine

ethanol

N-Boc-4-cyanophenylalanine

pentafluorophenol

4-methylmorpholine

→

title compound

Yield 92.0%

N-Boc-4-cyanophenylalanine-N-methylamide

Yield 92.0%

Solvents

CH2Cl2

Conditions

Workup

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

Procedure

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