Acetic Acid → HCID 117636219, compound

Participants

Reaction Steps

2-(N-Benzenecarbonyl)amino-6-amino-N-benzylhexanamide (105) (48 mg) obtained in Step 1-4 was dissolved in water (1.6 ml) and acetonitrile (1.1 ml). To the solution were added sodium nitrite (156 mg) and acetic acid (40.6 mg) under cooling with ice, and the mixture was stirred for 1 hour under cooling with ice. After 1 hour, the reaction liquid was warmed to room temperature and stirred for 1.5 hours. Subsequently, the reaction liquid was heated to 70° C. and stirred for an additional 20 minutes. The reaction liquid was concentrated and extracted with ethyl acetate (60 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: n-hexane:ethyl acetate=2:1 to n-hexane:ethyl acetate=1:6) to give a compound (106) (19.5 mg, yield: 41%) as a pale yellow solid. 1H NMR data on the compound (106) is shown below.

Provenance & Evidence