Reaktion #362475

Reaktionsgleichung

H2O

EtOAc

methyl L-phenylalaninate hydrochloride

methanesulfonyl chloride

→

N-(methylsulfonyl)-L-phenylalanine, methyl ester

Ausbeute 49.4%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting layers were separated
2. 2
   Waschenthe organic layer was washed with 3×200 mL of H2O
3. 3
   Sonstigedried
4. 4
   SonstigeThe resulting residue was chromatographed

Vorschrift

To a stirring solution of 2.51 g (20.0 mmol) of methyl L-phenylalaninate hydrochloride and 6.7 mL (48 mmol) of TEA in 50 mL of DMF was added 1.86 mL (24 mmol) of methanesulfonyl chloride. After 16 hours, the reaction mixture was added to 200 mL of H2O and 200 mL of EtOAc. The resulting layers were separated, and the organic layer was washed with 3×200 mL of H2O and dried. The resulting residue was chromatographed to yield 2.54 g (49%) of N-(methylsulfonyl)-L-phenylalanine, methyl ester (13), which was a clear colorless glass.

Quelle