反応 #6575

反応方程式

phenylalanine methyl ester

trifluoromethanesulfonic anhydride

2-n-butyl-1-(2-chlorophenyl)methyl-5-(2-hydroxyethyl)-1H-imidazole

diisopropylethylamine

→

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

収率 65.0%

溶媒

methylene chloride

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   workup.STIRRINGThis mixture was stirred for 2 hours at -78° C. and an additional 18 hours at ambient temperature
2. 2
   洗浄The reaction mixture was washed with water
3. 3
   その他dried
4. 4
   濃縮concentrated
5. 5
   その他chromatographed with 5% methanol in ethyl acetate

実験手順

A solution of trifluoromethanesulfonic anhydride (0.954 g, 3.38 mmol) in methylene chloride (5 ml) was cooled to -78° C. under nitrogen, and a solution of 2-n-butyl-1-(2-chlorophenyl)methyl-5-(2-hydroxyethyl)-1H-imidazole (0.9 g, 3.07 mmol), diisopropylethylamine (0.44 g. 3.38 mmol) and methylene chloride (10 ml) was added dropwise. The mixture was stirred at -78° C. for an additional 15 minutes, then a solution of the free base of phenylalanine methyl ester (prepared from 1.33 q (6.15 mmol) of the hydrochloride salt) in methylene chloride (10 ml) was added. This mixture was stirred for 2 hours at -78° C. and an additional 18 hours at ambient temperature. The reaction mixture was washed with water, dried and concentrated and the crude product was flash chromatographed with 5% methanol in ethyl acetate to yield 0.9 g (65%) of N-[2-{1-[(2 chlorophenyl)methyl]-2-n-butyl-1H-imidazol-5-yl}ethyl ]phenylalanine methyl ester.

出典