Hydrochloric Acid → 3-(naphthalene-2-sulfonamido)-3-phenylpropionic Acid

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Reaction Steps

4.13 g of 3-amino-3-phenylpropionic acid are dissolved in a mixture of 100 ml of dioxane and 25 ml of 1N NaOH, 5.6 g of 2-naphthalenesulphonyl chloride are added portionwise while maintaining a pH of 10.5–10.8 by addition of 1N NaOH, and the mixture is stirred for 2 hours at RT. The reaction mixture is diluted by adding 400 ml of water, acidified to pH 2 by adding 2N HCl, and extracted with EtOAc, the organic phase is washed with KHSO4/K2SO4 buffer solution and dried over Na2SO4, and the solvent is evaporated off under vacuum. 7.33 g of the expected product are obtained after triturating in heptane and drying under vacuum; m.p.=126–129° C.

Provenance & Evidence