P-Toluenesulfonamide → HCID 178427615, compound

Participants

Reaction Steps

To [7-(3-guanidino-propoxy)-2-oxo-1,2,3,4-tetrahydro-quinolin-3-yl]-acetic acid hydrochloride (0.90 g) was added para-toluenesulfonamide (0.65 g), 1-[3-(dimethylamino)-propyl]-3-ethylcarbodiimide hydrochloride (0.73 g), dimethylaminopyridine (0.05 g), and DMF (40 mL) and the resulting slurry formed a solution as it was stirred under N2 at room temperature for 21 days. The DMF was removed by vacuum distillation. The golden oil was triturated with CH2Cl2 (25 mL) followed by EtOAc (25 mL). The resulting oil was dissolved in 10 mL of 25% CH3CN/H2O and chromatographed on a C18 reverse phase column, eluting with a gradient of 10% CH3CN/H2O to 40% CH3CN/H2O to afford the title compound (73 mg) as an ivory solid after lyophilization.

Provenance & Evidence