3-Carboxybenzaldehyde → N-{3-[({[(2S)-1'-{2-[(5R)-3-[3,5-Bis(trifluoromethyl)benzoyl]-5-(4-fluorophenyl)-1,3-oxazolidin-5-yl]ethyl}-2,3-dihydrospiro[indene-1,4'-piperidin]-2-yl]oxy}acetyl)(methyl)amino]propyl}-3-formyl-N-methylbenzamide

Participants

Reaction Steps

The compound (150 mg, 0.193 mmol) obtained in Example 1k was dissolved in dichloromethane (6 mL), 3-formylbenzoic acid (43 mg, 0.289 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (63 mg, 0.289 mmol) and 4-N,N-dimethylaminopyridine (2 mg, 19.3 μmol) were added under ice cooling, and the mixture was stirred at the same temperature under a nitrogen atmosphere for 15 hours. After the reaction was completed, a saturated aqueous sodium hydrogencarbonate solution was added to the reaction mixture under ice cooling, and ethyl acetate was further added to separate the layers. The resulting organic layer was separated, washed with saturated sodium chloride solution, and then dried with anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:methanol, 10:1, v/v) to give the title compound (147 mg; yield, 83.8%) as a colorless oily substance.

Provenance & Evidence