Sodium Hydroxide → 4-Acetylamino-5-(3-methoxyphenyl)valeric acid

Participants

Reaction Steps

To a solution of tert-butyl 4-acetylamino-5-(3-methoxyphenyl)valerate (508 mg) in 1,4-dioxane (2 ml), 4N hydrogen chloride in 1,4-dioxane (4 ml) was added and the solution was stirred for 1 hour. The solution was poured into ice water (6 ml) and the pH of the solution was adjusted to 12 with sodium hydroxide solution. The solution was washed successively with diisopropyl ether and ethyl acetate and the pH of the solution was adjusted to 1 with 6N hydrochloric acid. The solution was extracted with ethyl acetate and the extract was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to give 4-acetylamino-5-(3-methoxyphenyl)valeric acid (362 mg).

Provenance & Evidence