Acetic Acid → HCID 59103926, compound

Participants

Reaction Steps

225 mg (0.5 mmol) of ethyl [(((1S,2S)-2-(((benzyloxy)carbonyl)amino)cyclohexyl)methyl)(t-butoxycarbonyl)-amino]acetate was dissolved in 10 ml of ethyl acetate. 30 mg of 10% palladium/carbon was added to the obtained solution, and they were stirred in the presence of hydrogen at room temperature overnight. The reaction solution was filtered through Celite. The solvent was evaporated, and the obtained crude product was dissolved in 10 ml of dichloromethane. 121 mg (0.67 mmol) of 4-(2,5-dihydro-1H-pyrrol-1-ylcarbonyl)benzaldehyde and 0.065 ml (1.14 mmol) of acetic acid were added to the obtained solution, and they were stirred at room temperature for 30 minutes. 310 mg (1.4 mmol) of sodium triacetoxyborohydride was added to the reaction mixture, and they were stirred at room temperature overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in a mixture of 2 ml of ethanol and 2 ml of 1 N sodium hydroxide, and the obtained solution was stirred at room temperature for 4 hours. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 5 ml of dichloromethane. 84 mg (0.5 mmol) of 2-chloro-1,3-dimethylimidazonium chloride and 0.14 ml (1.0 mmol) of triethylamine were added to the obtained solution, and they were stirred overnight. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 5 ml of 4N solution of hydrogen chloride in dioxane and the obtained solution was stirred at room temperature for 2 hours. The solvent was evaporated, and the obtained crude product was dissolved in 5 ml of dichloromethane. 0.062 ml (0.5 mmol) of 4-chlorobenzoyl chloride and 0.14 ml (1.0 mmol) of triethylamine were added to the obtained solution, and they were stirred at room temperature for 4 hours. The solvent was evaporated, and the obtained crude product was treated in the same manner as in step 3 in Example 1 to obtain the title compound.

Provenance & Evidence