Реакция #1605847

Уравнение реакции

cesium carbonate

chloromethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate

butyric acid

→

butyryloxymethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate

Растворители

ethyl acetate

dimethyl formamide

Условия реакции

Обработка

1. 1
   Другоеquenched with water/brine (1:1, 50 mL)
2. 2
   ЭкстракцияThe reaction was extracted with ethyl acetate (3×50 mL)
3. 3
   ПромывкаThe combined organics were washed with water (50 mL)
4. 4
   Сушкаbrine (50 mL) and dried (MgSO4)
5. 5
   Концентрированиеconcentrated
6. 6
   ДругоеThe crude product was purified by column chromatography on silica eluting with 010% tetrahydrofuran/dichloromethane with 1% Et3N
7. 7
   Другоеto give the product which
8. 8
   Другоеpurification
9. 9
   ДругоеThe product was purified by column chromatography on silica eluting with 0

Методика

To a solution of chloromethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate (1.20 g, 2.22 mmol) in dimethyl formamide (20 mL) was added butyric acid (0.30 mL, 3.33 mmol) followed by cesium carbonate (542 mg, 1.67 mmol). The reaction was then stirred at ambient temperature overnight. The reaction was diluted with ethyl acetate (50 mL) and quenched with water/brine (1:1, 50 mL). The reaction was extracted with ethyl acetate (3×50 mL). The combined organics were washed with water (50 mL) then brine (50 mL) and dried (MgSO4) and concentrated. The crude product was purified by column chromatography on silica eluting with 010% tetrahydrofuran/dichloromethane with 1% Et3N to give the product which required further purification. The product was purified by column chromatography on silica eluting with 0.51.5% Et3N/ethyl acetate to give butyryloxymethyl 7-(4-(4-(2,3-dichlorophenyl)piperazin-1-yl)butoxy)-2-oxo-3,4-dihydroquinoline-1(2H)-carboxylate, Compound-88 (348 mg, 26% over 2 steps).

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