Nitrogen → HCID 59819879, compound

Participants

Reaction Conditions

Reaction Steps

(The following reaction is done in an anhydrous N2 atmosphere.) Dissolve 4-[3-(3,4,5-Trimethoxy-phenyl)-propionylamino]-benzoic acid methyl ester (78) (45 mg, 0.12 mmol) in anhydrous DCM (1.2 mL), cool the solution to −78° C. and add dropwise BBr3 (90 μL, 0.96 mmol). Stir the reaction mixture for 30 min at −78° C. and after slowly warming up for additional 3 h at rt. Add dropwise ice-water/THF (1+1) followed by MeOH and remove solvent. Purify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95) to obtain 4-[3-(3,4,5-Trihydroxy-phenyl)-propionylamino]-benzoic acid (79) (17 mg, 44%) as a white solid. 1H NMR (400 MHz, CD3OD): 2.65 (t, 2H, J=7.5 Hz); 2.83 (t, 2H, J=7.5 Hz); 6.29 (s, 2H); 7.68 (d, 2H, J=8.3 Hz); 7.99 (d, 2H, J=8.6 Hz).

Provenance & Evidence