반응 #640720

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tert-Butyl 4-(3-(3-(1,3-dioxan-2-yl)propanoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzoate

Methyl 7-(4-(tert-butoxycarbonyl)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate

Sodium hydride

→

title compound

4-(3-(3-Carboxypropanoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzoic acid

용매

EtOAc

THF

THF

반응 조건

후처리

1. 1
   workup.STIRRINGthe reaction mixture was then stirred for 1 hour
2. 2
   workup.ADDITIONadded to a separatory funnel
3. 3
   기타partitioned with 3 N HCl (aqueous)
4. 4
   세척washed 2 times with 75 mL of brine (saturated, aqueous)
5. 5
   기타separated
6. 6
   건조dried over sodium sulfate
7. 7
   농축concentrated via rotary evaporation
8. 8
   기타to give initial product
9. 9
   기타The initial product was purified via flash chromatography (silica gel)

실험 절차

tert-Butyl 4-(3-(3-(1,3-dioxan-2-yl)propanoyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinolin-7-yl)benzoate. Methyl 7-(4-(tert-butoxycarbonyl)phenyl)-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate (452 mg, 1104 μmol) was dissolved in THF (11 mL). Sodium hydride (60% in oil, 442 mg, 11040 μmol) was then added, and the resulting mixture was stirred at room temperature for 1 hour. 2-[2-(1,3-Dioxanyl)]ethylmagnesium bromide in THF (2208 μL, 1104 μmol) was then added dropwise, and the reaction mixture was then stirred for 1 hour. The reaction mixture was diluted with 150 mL of EtOAc, added to a separatory funnel, partitioned with 3 N HCl (aqueous), washed 2 times with 75 mL of brine (saturated, aqueous), separated, dried over sodium sulfate, and concentrated via rotary evaporation to give initial product. The initial product was purified via flash chromatography (silica gel) to provide the title compound as a beige solid.

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