Hydrochloric Acid → HCID 118411577, compound

Participants

Reaction Steps

6-Amino-2-(4-phenylbenzenecarbonyl)amino-N-(4-chlorobenzyl)hexanamide hydrochloride (173) (1.29 g) was dissolved in water (50 ml) and acetonitrile (20 ml). To the solution were added sodium nitrite (4.02 g) and a solution of 4 N hydrochloric acid in 1,4-dioxane (3.31 ml) under cooling with ice, and the mixture was stirred for 1.0 hour under cooling with ice. After 1.5 hours, the reaction liquid was warmed to room temperature and stirred for 2.0 hours. The reaction liquid was concentrated and extracted with ethyl acetate (100 ml). The organic layer was washed with brine (100 ml), dried over anhydrous sodium sulfate, and filtered. After that, the filtrate was concentrated and the residue was purified by silica gel flash column chromatography (developing solvent: chloroform:methanol=100:1 to chloroform:methanol=30:1) to give a compound (175) (561 mg, yield: 47%) as a white solid. 1H NMR data on the compound (175) is shown below.

Provenance & Evidence