Valeryl chloride → HCID 10349732, compound

Participants

Reaction Steps

A solution of 78 mg (0.128 mmol) of 2-(5-amino-2-chlorophenyl)-4-[[2'-[N-(t-butoxycarbonyl)sulfamoyl]biphenyl-4-yl]methyl]-5-n-butyl-2,4-dihydro-3H-1,2,4-triazol-3-one (from Example 25), 76 μL (77 mg, 0.64 mmol) of valeryl chloride, and 15.6 mg (0.128 mmol) of 4-(dimethylamino)pyridine (DMAP) in 1 mL of dry pyridine was stirred overnight at room temperature. The mixture was quenched by addition of water and extracted twice with ethyl acetate. The combined organic fractions were washed twice with water, then with brine, and dried over Na2SO4. The filtered solution was concentrated, and the residue was flash chromatographed twice on silica gel (gradient elution with 0.5-3% methanol in CH2Cl2) to provide 41 mg (46%) of the title compound as a white solid, mp 177°-179° C.; homogeneous by TLC (9:1 CH2Cl2 --MeOH).

Provenance & Evidence