Trifluoroacetic acid → HCID 10166820, compound

Participants

Reaction Steps

3-(4-Acetylamino-2-{2-[4-(N′,N′-dimethyl-hydrazinocarbonyl)-naphthalen-1-yl]-ethoxy}-benzenesulfonylamino)-4,4-diethyoxy-butyric acid tert-butyl ester (0.12 g, 0.17 mmol) was stirred in 12 mL of a solution of 17% TFA in CH2Cl2 at room temperature for 2 h. Analytical HPLC indicated the reaction was complete. The reaction mixture was concentrated. Residual TFA was azeotroped with toluene. Half of the product was lyophilized to give (0.06 g, 54%). The second half of the crude product was stirred with 22 mL of a solution of 10% TFA in 1:1 acetonitrile/water for 16 h. Analytical HPLC indicated that reaction was complete. The reaction mixture was diluted with H2O and lyopholyzed. The crude product was purified by preparative-scale reverse phase HPLC (0 to 30% acetonitrile in H2O with 0.1% TFA over 2 h at 15 mL/min on Vydac #218TP152022-2.5×25 cm C18 column) and then lyophilized to give (0.035 g, 0.06 mmol, 36%) of 3-(4-Acetylamino-2-{2-[4-(N′,N′-dimethyl-hydrazinocarbonyl)-naphthalen-1-yl]-ethoxy}-benzenesulfonylamino)-4-oxo-butyric acid as a fluffy white solid. MS m/z 571 (M+1).

Provenance & Evidence