Triethylamine → HCID 86589886, compound

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Reaction Steps

2.5 g (13.8 mmol) of 3-methoxy-2-nitrobenzaldehyde was dissolved in a mixture of 70 ml of ethanol and 70 ml of THF. 1.0 g (27.6 mmol) of sodium borohydride was added to the obtained solution. They were stirred at room temperature overnight. After the treatment with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 100 ml of dichloromethane. 1.3 ml (16.6 mmol) of methanesulfonyl chloride and 2.9 ml (20.7 mmol) of triethylamine were added to the obtained solution, and they were stirred under cooling with ice for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 70 ml of ethanol. 2.9 g (20.7 mmol) of glycine ethyl ester hydrochloride and 2.3 g (27.6 mmol) of sodium hydrogencarbonate were added to the obtained solution, and they were stirred at 70° C. for 6 hours. The solvent was evaporated. After the extraction with ethyl acetate as the extracting solvent by an ordinary method, the obtained crude product was dissolved in 100 ml of dichloromethane. 2.0 ml (15.6 mmol) of 4-chlorobenzoyl chloride and 2.7 ml (19.5 mmol) of triethylamine were added to the obtained solution under cooling with ice, and they were stirred under cooling with ice for 2 hours. After the treatment with dichloromethane as the extracting solvent by an ordinary method, the obtained crude product was purified by the silica gel column chromatography to obtain the title compound.

Provenance & Evidence