反応 #446908

反応方程式

dimethylamine

HCl

HCl

hydroxybenzotriazole

3-indolepyruvic acid

→

N,N-dimethyl 3-indolepyruvamide

溶媒

CH2Cl2

tetrahydrofuran

4-methylmorpholine

tetrahydrofuran

反応条件

後処理

1. 1
   workup.DISSOLUTIONAfter dissolving
2. 2
   その他leaving the bath temperature
3. 3
   その他to rise up to room temperature
4. 4
   洗浄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
   ろ過this was filtered off
7. 7
   その他the mixture was purified by flash chromatography (silica gel, eluent CH2Cl2 25/n-propanol 1,5)

実験手順

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).

出典