Methanesulfonyl chloride → Methyl 2-(methyl(4-(methylsulfonamido)benzyl)amino)acetate

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Reaction Steps

A solution of methyl 2-((4-aminobenzyl)(methyl)amino)acetate (0.680 g, 3.27 mmol) in pyridine (15 ml) was cooled to 0° C., and methane sulfonylchloride (0.280 ml, 3.59 mmol) was added. The mixture was warmed to RT and stirred for 1 hour. The solvent was removed, and the crude was portioned between DCM and water. The aqueous phase was basified with solid K2CO3 and extracted with EtOAc. The combined organic layers were dried over Na2SO4, and the solvent was evaporated. The crude was filtered on SCX cartridge (DCM/MeOH 1/1; MeOH/conc.aq.NH4OH 90/10). The basic fraction was evaporated to dryness to give methyl 2-(methyl(4-(methylsulfonamido)-benzyl)amino)acetate (0.750 g, 2.62 mmol, 80% yield, MS/ESI+ 287.2 [MH]+).

Provenance & Evidence