Nitrogen → HCID 16004686, compound

Participants

Reaction Conditions

Reaction Steps

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve 3-[2-(2,4,6-Trimethoxy-phenyl)-acetylamino]-benzoic acid (17) (134 mg, 0.39 mmol) in anhydrous DCM (5.3 mL), cool the solution to −78° C. and add dropwise BBr3 (240 μL, 2.55 mmol). Stir the reaction mixture for 30 min at −78° C. and after slowly warming up for additional 2 h at rt. Add dropwise ice water, separate layers and extract aqu. layer with EtOAc (3 times). Wash combined organic layer with brine and dry with Na2SO4. Purify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95) to obtain 3-[2-(2,4,6-Trihydroxy-phenyl)-acetylamino]-benzoic acid (18) (29 mg, 22%) as a yellowish solid. 1H NMR (400 MHz, CD3OD): 3.69 (s, 2H); 5.97 (s, 2H); 7.43 (t, 1H, J=8.0 Hz); 7.76 (br.dd, 1H, J1=7.6 Hz); 7.84 (br.dd, 1H, J1=8.1 Hz); 8.17 (t, 1H, J=1.8 Hz).

Provenance & Evidence