Sodium Carbonate → 5-({[7-({2-[(7-{[(3-Carboxy-4-hydroxyphenyl)amino]sulfonyl}(2-naphthyl)) amino]-ethyl}-amino)(2-naphthyl)]sulfonyl}amino)-2-hydroxybenzoic acid

Participants

Reaction Steps

To 64 mg (0.08 mmol) of compound 120 was added 20 mL of saturated sodium carbonate, 76 mg of sodium hydrosulfite (Na2S2O4), and 2 mL of DMF. The reaction was allowed to stir at ambient temperature for 22 hours. Then, the reaction was extracted with ethyl acetate and 1 N HCl. The organic layer was dried (MgSO4), filtered, and the volatiles removed by rotary evaporation. The product was purified by reverse-phase HPLC (C18, 250×20 mm column) using trifluoroacetic acid (TFA) buffer system (Buffer A: 5% acetonitrile, 95% water, 0.05% TFA; Buffer B: 95% acetonitrile, 5% water, 0.05% TFA; 17 mL/min; 0–50% B in 10 min., 50% B for 17 min., 50–100% B in 20 min). Fractions containing the product were combined and lyophilized to provide 24 mg of compound 121.

Provenance & Evidence