Reaktion #64405

Reaktionsgleichung

methylamine

ethanol

N-Boc-4-cyanophenylalanine

pentafluorophenol

4-methylmorpholine

→

title compound

Ausbeute 92.0%

N-Boc-4-cyanophenylalanine-N-methylamide

Ausbeute 92.0%

Lösungsmittel

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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%).

Quelle