Nitrogen → HCID 59819881, compound

Participants

Reaction Conditions

Reaction Steps

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve 3-{3-[3-(3,4,5-Trimethoxy-phenyl)-propionylamino]-phenylamino-benzoic acid methyl ester (91) (36 mg, 0.08 mmol) in anhydrous DCM (2.3 mL) at −78° C., add dropwise a 1M solution of BBr3 in DCM (930 μL, 0.93 mmol) and stir for additional 30 min at −78° C. After slowly warming up stir the reaction solution for additional 4 h at rt. Cool reaction mixture to 0° C., add dropwise water/THF (1+1) and remove solvent. Purify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95) to obtain 3-{3-[3-(3,4,5-Trihydroxy-phenyl)-propionylamino]-phenylamino}-benzoic acid (92) (10 mg, 33%) as a white solid. 1H NMR (400 MHz, CD3OD): 2.60 (t, 2H, J=7.7 Hz); 2.85 (t, 2H, J=7.7 Hz); 6.29 (s, 2H); 6.70 (dd, 1H, J1=8.0 Hz, J2=2.0 Hz); 7.06 (d, 1H, J=8.0 Hz), 7.21 (t, 1H, J=8.0 Hz), 7.33-7.37 (m, 2H), 7.45 (mc, 1H); 7.50-7.54 (m, 1H); 7.77 (s, 1H).

Provenance & Evidence