Lithium Hydroxide → 3-(((Tert-butoxy)carbonyl)amino)benzoic acid

Participants

Reaction Conditions

Reaction Steps

To the crude 3-tert-butoxycarbonylamino-benzoic acid ethyl ester (˜2.0 g, 0.00754 mmol) added THF (15 mL), and 0.5M LiOH (15 mL). The mixture was heated for two hours at 75° C. and the THF was removed in vacuo after cooling. The precipitate was filtered from the remaining mixture and the filtrate was transferred to a separatory funnel. The aqueous layer was washed with dichloromethane (3×) and was acidified to pH˜5 using 1M HCl. The product was then extracted with ethyl acetate, washed with water, saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated. 730 mg of 3-tert-Butoxycarbonylamino-benzoic acid (white solid) was isolated. 1H NMR (DMSO-d6) δ (ppm): 9.58 (s, 1H), 8.16 (s, 1H), 7.63 (d, 1H), 7.54 (d, 1H), 7.37 (t, 1H), 1.49 (s, 9H)

Provenance & Evidence