N-Tosyl-L-alanine

56-41-7

98-59-9

4816-81-3

GENERAL STEPS: The synthesis was carried out using the N-toluene sulfonylation method reported in the literature. In a round-bottomed flask, 2.4 equivalents of Na2CO3 was dissolved in water at 70 °C (concentration 0.66 mol/L). Subsequently, 1.0 equiv. of L-alanine was added, followed by the slow addition of 1.4 equiv. of p-toluenesulfonyl chloride. The resulting suspension was stirred and reacted at 70 °C for 40 min, followed by warming to 85 °C and continued stirring for 5 min. Upon completion of the reaction, the reaction mixture was filtered directly and the solids were washed with hot water at 85°C. The filtrate was cooled to room temperature and acidified with 6 M aqueous HCl to pH=1. The precipitated solid product was collected by filtration and dried under vacuum. The resulting 2-(4-methylphenylsulfonamido)propionic acid was used for subsequent experiments without further purification.