反応 #1483090

反応方程式

DDAIP

4

dodecyl 2-(dimethylamino)propanoate

methane sulfonic acid

→

dodecyl 2-(dimethylamino)propanoate methane sulfonate salt

収率 97.3%

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
   workup.STIRRINGstirred at RT for ½ h (No solid)
4. 4
   濃縮The reaction mixture was concentrated under vacuum
5. 5
   その他flushed with hexane (3×30 mL)

実験手順

A stirred solution of DDAIP base 4 (85 g, 298 mmol) in ethyl acetate (500 mL) was cooled to 0° C., then methane sulfonic acid 18 (28.6 g, 298 mmol) was added in one lot. After addition, the temperature of the reaction mixture was slowly raised to RT and stirred at RT for 48 h; the reaction mixture was monitored by TLC. The reaction mixture was concentrated under vacuum. The obtained residue was taken in n-hexane (30 mL) and stirred at RT for ½ h (No solid). The reaction mixture was concentrated under vacuum and flushed with hexane (3×30 mL) to afford dodecyl 2-(dimethylamino)propanoate methane sulfonate salt (19, Nex-22) (110 g, yield: 97.34%) as a solid, mp: 66-72° C. 1H-NMR (400 MHz, CDCl3): δ 0.9 (t, 3H), 1.35 (m, 18H), 1.65 (q, 2H), 1.7 (d, 3H), 2.8 (s, 3H), 3 (s, 6H), 4.15 (q, 1H), 4.2 (t, 2H); LCMS: 286 (M+); HPLC: 100%.

出典