تفاعل #446908

معادلة التفاعل

dimethylamine

HCl

HCl

hydroxybenzotriazole

3-indolepyruvic acid

→

N,N-dimethyl 3-indolepyruvamide

المذيبات

CH2Cl2

tetrahydrofuran

4-methylmorpholine

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.DISSOLUTIONAfter dissolving
2. 2
   أخرىleaving the bath temperature
3. 3
   أخرىto rise up to room temperature
4. 4
   غسيلthe 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
   ترشيحthis was filtered off
7. 7
   أخرىthe mixture was purified by flash chromatography (silica gel, eluent CH2Cl2 25/n-propanol 1,5)

الإجراء التجريبي

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).

المصدر