Triethylamine → HCID 68833740, compound

Participants

Reaction Steps

A mixture of 3-{[(tert-butoxycarbonyl)amino]methyl}-2-isobutyl-4-(4-methylphenyl)quinoline-6-carboxylic acid (Example 45(1)) (2.24 g, 5.0 mmol), diphenylphosphoryl azide (1.3 ml, 6.0 mmol), triethylamine (0.84 ml, 6.0 mmol) and N,N-dimethylformamide (20 ml) was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and toluene (30 ml) was added to the residue. The mixture was heated under reflux for 1 hr. The obtained mixture was cooled to room temperature and 9-fluorenylmethanol (1.47 g, 7.5 mmol) was added. The mixture was heated under reflux for 12 hrs. The reaction mixture was poured into water and extracted with ethyl acetate. The extract was 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 9H-fluoren-9-ylmethyl 3-[[(tert-butoxycarbonyl)amino]methyl]-2-isobutyl-4-(4-methylphenyl)-6-quinolinylcarbamate (1.45 g, yield 45%) as an amorphous form.

Provenance & Evidence