反应 #77478

反应方程式

(±)-7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline

L-pyroglutamic acid

→

(+)-7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline L-pyroglutamate

收率 42.0%

溶剂

ethanol

反应条件

后处理

1. 1
   温度heated
2. 2
   其他to form a uniform solution
3. 3
   温度to cool gradually
4. 4
   其他The crystal precipitated
5. 5
   过滤was recovered by a filtration
6. 6
   洗涤washed with ethanol

实验过程

A solution of (±)-7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline (7.1 g) in ethanol (85 ml) was combined with L-pyroglutamic acid (2.72 g) and heated to form a uniform solution. The mixture was allowed to stand to cool gradually, and stirred at room temperature for 14 hours. The crystal precipitated was recovered by a filtration and washed with ethanol to obtain (+)-7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline L-pyroglutamate (4.1 g). This crystal was suspended in methanol (50 ml) and combined with a 28% solution of sodium methoxide in methanol (1.7 g) and then the solvent was distilled off under reduced pressure. The resultant crystal was washed with water and dried to obtain a crystal (3.1 g). This was dissolved in ethanol (20 ml) and combined with methanesulfonic acid (1.8 g). The solvent was distilled off under reduced pressure, and the resultant crystal was recrystallized from ethanol to obtain (+)-7-(2-chloro-5-fluorophenyl)-5-guanidinoimino-4-methyl-5,6,7,8-tetrahydroquinoline methanesulfonate (Compound H)(3.6 g, 99.3% ee).

来源