반응 #964358

반응 방정식

Water

triethylamine

cyclopentyl{4-[(5-oxo-2-phenyl-5,6-dihydro-4H-1,3,4-oxadiazin-4-yl)methyl]phenyl}acetyl chloride

methyl 4-amino-2,3-dihydro-1H-indene-2-carboxylate

→

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

용매

dichloromethane

dichloromethane

반응 조건

후처리

1. 1
   workup.ADDITIONwere added to the mixture
2. 2
   추출the reaction solution was extracted with dichloromethane
3. 3
   건조The combined organic phases were dried over sodium sulfate
4. 4
   농축concentrated on a rotary evaporator
5. 5
   기타The residue was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 3:1→1:1)

실험 절차

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.

출처