洛索洛芬杂质18

反应条件: temp:0.00; pressure:0.00; stir:

实验步骤: 投料: 将原料溶于乙腈中，加入TEMPO，rt下搅拌7h； 点板没有反应，搅拌过周末； 点板没有反应，反应舍弃。

实验步骤: 投料: 将原料溶于2mL水中，无法溶清，加入1mLDMF，加入双氧水，加入4甲基哌啶氧化物，70℃搅拌5h； 期间点板均无新点生成，搅拌过夜； 有新点生成，但大部分原料，后处理，用水和EA萃取，有机相干燥过滤旋蒸，得到粗品，核磁鉴定结构，大部分原料。

实验步骤: 投料: 将原料溶于62mL盐酸甲醇溶液（4M,3.0eq）中，rt下搅拌 5h； 点板原料反应完全，旋干溶剂，用水和EA进行萃取，有机相干燥过滤旋蒸，得到淡黄色液体20g，核磁鉴定结构正确。

实验步骤: 投料: 将原料溶于DMF中，加入高碘酸钠，150℃搅拌2h； 大部分原料反应完全，自然冷却至室温，用水和EA进行萃取，有机相干燥过滤旋蒸，得到粗产品红色油状物4.6g； 柱层析纯化，PE:EA=10:1; 拿到红棕色液体2.0g，核磁鉴定结构有一半是产品，另一半为羟基产品；

实验步骤: 投料: 将原料溶于DMF中，加入高碘酸钠，150℃回流，搅拌5h； 点板大部分反应完全，后处理，用水和EA进行萃取，有机相干燥过滤旋蒸，得到粗品，爬大板，PE:EA=10:1； 分别送HPLC,GC-MS和核磁鉴定结构，HPLC只有一组峰，GC-MS有几重峰，同时通过核磁鉴定，判断产品中含有形成羟基的产物，有2/3为产品点。

实验步骤: 投料: 将原料溶于DMF中，加入高碘酸钠，100℃回流，搅拌3h； 点板大部分原料反应完全，后处理，自然冷却至室温，用水和EA进行萃取，有机相干燥过滤旋蒸，得到黄色液体； 核磁鉴定结构有1/3是形成羟基，剩下是产品。

实验步骤: 投料: 将原料溶于16mL盐酸甲醇溶液（4M,3.0eq）中，rt搅拌2h； 点板原料反应完全，旋干溶剂，盐酸甲醇中含有不少水分，用EA萃取，有机相干燥过滤旋蒸，得到淡黄色液体4.87g核磁鉴定结构正确。

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was prepared according to the procedure of example 41, substituting 3-(8-chloro-3-methyl-quinolin-4-yl)-phenol and 2-(4-bromomethyl-phenyl)-propionic acid methyl ester. Purification by supercritical fluid chromatography (MeOH/CO2). Electronic circular dichroism CD λmax=−4 mdeg @ 225 nm (EtOH). MS (ESI) m/z 432. This compound was prepared Purification by supercritical fluid chromatography (MeOH/CO2)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was prepared according to the procedure of example 41, substituting 3-(8-chloro-3-methyl-quinolin-4-yl)-phenol and 2-(4-bromomethyl-phenyl)-propionic acid methyl ester. Purification by supercritical fluid chromatography (MeOH/CO2). Electronic circular dichroism CD λmax=+6 mdeg @ 226 nm (EtOH). MS (ESI) m/z 432. This compound was prepared Purification by supercritical fluid chromatography (MeOH/CO2)

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: This compound was prepared according to the procedure of example 41, substituting 3-(8-chloro-3-methyl-quinolin-4-yl)-phenol and 2-(4-bromomethyl-phenyl)-propionic acid methyl ester. MS (ESI) m/z 432. This compound was prepared

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 4-Cyano-3-tetrahydrothiophenone (5.0 g) was dissolved in N,N-dimethylformamide (30 ml), then, sodium hydride (oil, about 60%, 950 mg) was added under ice cooling, and stirred at the same temperature for 30 minutes. Then, to the mixture was added a solution of methyl 2-(4-bromomethylphenyl)propionate (10.1 g) in N,N-dimethylformamide (10.0 ml) under ice cooling, and the reaction mixture was stirred overnight at room temperature. The reaction mixture was quenched with water, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and then dried over sodium sulfate. The solvent was evaporated under reduced pressure, and then the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1) to give the title compound (5.5 g, 46%). the reaction mixture was stirred overnight at room temperature The reaction mixture was quenched with water extracted with ethyl acetate The organic layer was washed with water and saturated brine dried over sodium sulfate The solvent was evaporated under reduced pressure the residue was purified by silica gel column chromatography (hexane/ethyl acetate=5/1)