Cysteamine Hydrochloride → (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-phenylacetic acid

Participants

Reaction Steps

To a 50 mL round-bottom flask charged with a solution of sodium bicarbonate (78.0 mg, 0.93 mmol) in 4.5 mL water was added 2-aminoethanethiol hydrochloride (56.6 mg, 0.50 mmol). To this stirring solution was added dropwise over 60 seconds a solution of 25j (114.8 mg, 0.45 mmol) in 4.5 mL CH2Cl2. The reaction was vigorously stirred for 25 minutes at room temperature, then extracted twice with fresh CH2Cl2. The combined CH2Cl2 extracts were washed once with 5% aqueous HCl, once with 10% aqueous sodium bicarbonate, then once with water. The organic fraction was dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford 132.3 mg (86% from 24j) of 26j as an off-white paste.

Provenance & Evidence