Methanesulfonyl chloride → (2R)-N-methanesulfonyl-(4-chlorophenyl)alanine methyl ester
Reaction equation
[CH3:1][O:2][C:3](=[O:14])[C@@H:4]([CH3:13])[NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:14])[C@@H:4]([CH3:13])[N:5]([C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[CH:8][CH:7]=1)[S:16]([CH3:15])(=[O:18])=[O:17]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of (2R)-4-chlorophenylalanine methylester (213 mg, 1.00 mmol) in DCM (5 mL) was added dropwise TEA (280 μl, 2.00 mmol) and then methanesulfonylchloride (100 μl, 1.3 mmol) at 0° C. After 30 min, the reaction mixture was quenched with water and extracted with DCM and EtOAc. The organic solution was washed with 1N HCl, dried over MgSO4 and concentrated in vacuo, and the residue was purified by column chomatography (MeOH/CHCl3=1/25) to give the title compound (280 mg, 96.1%).