Triethylamine → HCID 90779904, compound

Participants

Reaction Steps

To a mixture of tert-butyl [6-(hydroxymethyl)-2-isobutyl-4-(4-methylphenyl)quinolin-3-yl]methylcarbamate (1.1 g, 2.5 mmol), triethylamine (0.53 ml, 3.8 mmol) and tetrahydrofuran (50 ml) was added methanesulfonyl chloride (0.3 ml, 3.8 mmol) under ice-cooling, and the mixture was stirred for 30 min. A mixture of ethyl thioglycollate (0.42 ml, 3.8 mmol), sodium hydride (60% in oil, 0.15 g, 3.8 mmol) and N,N-dimethylformamide (3 ml) were added to the reaction mixture and the mixture was stirred at room temperature for 15 min. The reaction mixture was partitioned between ethyl acetate and water and the aqueous layer was extracted with ethyl acetate. The organic layer and the extract were combined, washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography to give ethyl ({[3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinolin-6-yl]methyl}thio)acetate (1.1 g, yield 83%) as a white powder.

Provenance & Evidence