反応 #6573

反応方程式

diisopropylamine

n-butyl lithium

[{1-[(2-chlorophenyl)methyl]-2-n-butyl-1H-imidazol-5-yl}methylene]phenylalanine methyl ester

methyl iodide

→

N-[{1-[(2-chlorophenyl)-methyl]-2-n-butyl-1H-imidazol-5-yl}methylene]-α-methylphenyl-alanine methyl ester

溶媒

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   温度the solution was cooled to -78° C.
2. 2
   workup.STIRRINGThe mixture was stirred for 30 minutes at -78° C. under argon
3. 3
   温度to slowly warm to ambient temperature
4. 4
   workup.STIRRINGstirred for 18 hours
5. 5
   その他The solvent was evaporated
6. 6
   workup.DISSOLUTIONthe residue dissolved in ethyl acetate
7. 7
   ろ過the insoluble materials were filtered
8. 8
   その他the concentrated product was used without purification

実験手順

To a solution of diisopropylamine (1.27 g, 12.6 mmol) in tetrahydrofuran (50 ml) was added n-butyl lithium (5 ml of 2.5M in hexane, 12.6 mmol) at 0° C. After being stirred at 0° C. for 15 minutes, the solution was cooled to -78° C. and a solution of the imine, N [{1-[(2-chlorophenyl)methyl]-2-n-butyl-1H-imidazol-5-yl}methylene]phenylalanine methyl ester (Example 3(i) Method B) (5.51 g, 12.6 mmol) in tetrahydrofuran (35 ml) was added dropwise. The mixture was stirred for 30 minutes at -78° C. under argon and methyl iodide (2.06 q, 14.5 mmol) in tetrahydrofuran (15 ml) was added at 78° C. The mixture was allowed to slowly warm to ambient temperature and then stirred for 18 hours. The solvent was evaporated, the residue dissolved in ethyl acetate, the insoluble materials were filtered and the concentrated product was used without purification to give 8N18 g of N-[{1-[(2-chlorophenyl)-methyl]-2-n-butyl-1H-imidazol-5-yl}methylene]-α-methylphenyl-alanine methyl ester.

出典