Nitrogen → 5-{2-Amino-4-[2-(3,4,5-trihydroxy-phenyl)-acetylamino]-phenyl}-2-methyl-furan-3-carboxylic acid

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Reaction Steps

(The following reaction is done in an N2 atmosphere.) Dissolve 2-Methyl-5-{2-nitro-4-[2-(3,4,5-trihydroxy-phenyl)-acetylamino]-phenyl}-furan-3-carboxylic acid (61) (21 mg, 0.05 mmol) in MeOH (1.5 mL) and add Pd on carbon (10% (w/w) Pd content, 11.5 mg, 0.005 mmol) followed by NH4CO2H (68 mg, 1.08 mmol) at rt. Degas the reaction mixture carefully (flush with N2) and stir it for 17 h at rt. Filtrate reaction mixture through a short pad of celite and remove solvent. Purify the crude product by preparative RP HPLC (gradient, water/CH3CN 95:5 to 5:95) to obtain 5-{2-Amino-4-[2-(3,4,5-trihydroxy-phenyl)-acetylamino]phenyl}-2-methyl-furan-3-carboxylic acid (62) (4.6 mg, 23%) as a white solid. 1H NMR (400 MHz, CD3OD): 2.69 (s, 3H); 3.50 (s, 2H); 6.39 (s, 2H); 6.91 (s, 1H); 7.13 (br.d, 1H, J=8.6 Hz); 7.57 (d, 1H, J=8.6 Hz) 7.65 (br.s, 1H).

Provenance & Evidence