4-Methoxybenzenesulfonyl chloride → Methyl 3-hydroxy-2-(4-methoxybenzenesulfonylamino)propionate

Participants

Reaction Conditions

Reaction Steps

To a mixture of 5.0 g (32.14 mmol) of D, L-serine methyl ester and 15.7 mL (0.012 mol) of triethylamine in 100 mL of dichloromethane, cooled to 0° C., was added 6.64 g (32.14 mmol) of 4-methoxybenzenesulfonyl chloride. The mixture was then stirred under argon at room temperature for two days. The mixture was diluted with 100 mL of dichloromethane and then washed with 60 mL each of water, 2N citric acid and brine and than dried over Na2SO4. The solvent was removed under vacuum to give a solid which was recrystallized from ethyl acetate to give 5.0 g (54%) of the product as white crystals, m.p. 92-94° C.

Provenance & Evidence