反应 #446908

反应方程式

dimethylamine

HCl

HCl

hydroxybenzotriazole

3-indolepyruvic acid

→

N,N-dimethyl 3-indolepyruvamide

溶剂

CH2Cl2

tetrahydrofuran

4-methylmorpholine

tetrahydrofuran

反应条件

后处理

1. 1
   workup.DISSOLUTIONAfter dissolving
2. 2
   其他leaving the bath temperature
3. 3
   其他to rise up to room temperature
4. 4
   洗涤the organic solution was washed in sequence with 5% NaHCO3 (10×25 ml), saturated NaCl solution (3×25 ml), 5% KHSO4 (10×25 ml) and saturated NaCl solution up to neutrality
5. 5
   workup.WAITAfter standing for one night on anhydrous Na2SO4
6. 6
   过滤this was filtered off
7. 7
   其他the mixture was purified by flash chromatography (silica gel, eluent CH2Cl2 25/n-propanol 1,5)

实验过程

A solution of 500 mg 3-indolepyruvic acid in 25 ml anhydrous tetrahydrofuran on an ice-salt bath, under argon atmosphere and under stirring was additioned in swift succession with: 400 mg hydroxybenzotriazole (HOBt) and 570 mg 1-(3-dimethylaminopropyl)-3-ethylcarbimdie.HCl (EDC.HCl). After dissolving and still maintaining the ice-salt bath, 240 mg dimethylamine.HCl were added dissolved in 10 ml anhydrous tetrahydrofuran and 325 microliters 4-methylmorpholine (NMM). The yellowish gold solution was maintained under stirring for one night, leaving the bath temperature to rise up to room temperature. The volume was then tripled adding CH2Cl2 and the organic solution was washed in sequence with 5% NaHCO3 (10×25 ml), saturated NaCl solution (3×25 ml), 5% KHSO4 (10×25 ml) and saturated NaCl solution up to neutrality. After standing for one night on anhydrous Na2SO4, this was filtered off, the mixture was purified by flash chromatography (silica gel, eluent CH2Cl2 25/n-propanol 1,5).

来源