反応 #1483091

反応方程式

DDAIP

4

dodecyl 2-(dimethylamino)propanoate

ethane sulfonic acid

→

dodecyl 2-(dimethylamino)propanoate ethane sulfonate salt

収率 98.4%

溶媒

ethyl acetate

反応条件

後処理

1. 1
   workup.ADDITIONAfter addition
2. 2
   濃縮The reaction mixture was concentrated under vacuum
3. 3
   その他flushed with hexane
4. 4
   workup.STIRRINGstirred at RT for 2 h (No solid)
5. 5
   workup.WAITThe obtained sticky solid kept in deep freezer for 12 h

実験手順

A stirred solution of DDAIP base 4 (85 g, 298 mmol) in ethyl acetate (600 mL) was cooled to 0° C., then ethane sulfonic acid 20 (32.79 g, 298 mmol) was added in one lot. After addition, the temperature of the reaction mixture was slowly raised to RT, stirred at RT for 12 h and the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum and flushed with hexane. The obtained residue was taken in n-hexane (200 mL) and stirred at RT for 2 h (No solid). The obtained sticky solid kept in deep freezer for 12 h to afford dodecyl 2-(dimethylamino)propanoate ethane sulfonate salt (21, Nex-30) (116 g, yield: 98.4%) as a hygroscopic solid, Mp: 45-50° C. 1H-NMR (400 MHz, CDCl3): δ 0.9 (t, 31H), 1.3 (m, 18H), 1.35 (t, 3H), 1.7 (d, 31H), 1.8 (q, 21H), 2.9 (q, 2H), 3 (m, 6H), 4.2 (m, 2H), 4.2 (m, 1H); LCMS: 286 (M++1); HPLC: 99.47%.

出典