2-Naphthalenesulfonyl chloride → (R)-3-(Naphthalene-2-sulfonamido)-3-phenylpropanoic Acid

Participants

Reaction Steps

To a solution of (R)-ethyl 3-amino-3-phenylpropanoate hydrochloride (5.04 g, 21.9 mmol) and naphthalene-2-sulfonyl chloride (4.97 g, 21.9 mmol) in CH2Cl2 (60 mL) was added a solution of Et3N (7.65 mL, 54.9 mmol) in CH2Cl2 (60 mL) at 0° C. over a period of 45 min. The reaction mixture was stirred at room temperature for 42 h and then washed with aqueous 1 M HCl (300 mL). The organic layer was dried (Na2SO4) and evaporated to dryness, which gave 8.05 g (96%) of S9-1 as a light pink solid.

Provenance & Evidence