反应 #1914860

反应方程式

NaHCO3

3-3a

(2-Methoxy-pyrimidin-5-yl)-5-oxo-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-nonanoic acid ethyl ester

1,2-ethanedithiol

BF3.OEt2

→

desired product 4-1a

(2-methoxy-pyrimidin-5-yl)-4-{2-[4-(5,6,7,8-tetrahydro-1,8-naphthyridin-2-yl)butyl]-1,3-dithiolan-2-yl}butanoic acid ethyl ester

溶剂

AcOH

反应条件

后处理

1. 1
   workup.WAITat rt for 3.5 hr
2. 2
   workup.ADDITIONThe reaction mixture was slowly poured into ice-
3. 3
   萃取extracted with diethyl ether (2×200 mL)
4. 4
   洗涤washed with brine
5. 5
   干燥dried over Na2SO4
6. 6
   其他After removal of the solvent
7. 7
   其他the residue was purified by flash chromatography on silica gel (100% EtOAc)

实验过程

To a mixture of 3-3a (7.6 g, 17.4 mmol) and 1,2-ethanedithiol (17.5 mL, 208.6 mmol) in 25 mL AcOH was added BF3.OEt2 (17.5 mL, 138.1 mmol) dropwise at 0° C. under nitrogen. The reaction mixture was stirred at 0 C for 0.5 hr, then at rt for 3.5 hr. The reaction mixture was slowly poured into ice-cooled 300 mL NaHCO3 (sat.) and extracted with diethyl ether (2×200 mL). The organic layers were combined and washed with brine and dried over Na2SO4. After removal of the solvent, the residue was purified by flash chromatography on silica gel (100% EtOAc) to afford the desired product 4-1a as an oil.

来源