Water → Methyl 4-[(cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl)amino]-2,3-dihydro-1H-indene-2-carboxylate

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Reaction Steps

337 mg (0.821 mmol) of cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl chloride (enantiomer 1; Example 81A) were dissolved in 8 ml of dichloromethane, and 83 mg (0.821 mmol) of triethylamine were added. 157 mg (0.821 mmol) of methyl 4-amino-2,3-dihydro-1H-indene-2-carboxylate (enantiomer 1; Example 89A), dissolved in 2 ml of dichloromethane, were added to the mixture. The mixture was stirred at room temperature overnight. Water was then added, and the reaction solution was extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated on a rotary evaporator. The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 3:1→1:1). This gave 182 mg (0.32 mmol, 39% of theory) of the title compound.

Provenance & Evidence