Triethylamine → N-Boc-4-hydroxy-D-homophenylalanine

Participants

Reaction Steps

To a stirred solution of (2R)-4-(4-hydroxyphenyl)-2-amino-butanoic acid hydrobromide (5.0 g, 18.18 mmol) and triethylamine (5.25 mL, 2 eq) in dioxane (50 mL) and water (50 mL) at 0° C. was added a solution of 2-(tert-butoxycarbonyloxyimino)-2-phenylacetonitile (BOCON) (4.9 g) in dioxane (10 mL). The reaction mixture was allowed to warm up to room temperature and stirred for five hours when it became homogeneous: The reaction mixture was diluted with ethyl acetate (EtOAc) and the organic was seperated. The aqueous layer was acidified with citric acid (20%) and extracted with EtOAc. The combined organics were washed with brine, dried over magnesium sulfate, filtered and evaporated to give the desired material.

Provenance & Evidence