反応 #1483086

反応方程式

DDAIP

4

dodecyl 2-(dimethylamino)propanoate

citric acid

→

dodecyl 2-(dimethylamino)propanoate citrate salt

収率 95.6%

溶媒

methanol

反応条件

後処理

1. 1
   workup.ADDITIONAfter addition
2. 2
   濃縮The solvent was concentrated under vacuum
3. 3
   workup.ADDITIONThe residue was diluted with n-hexane (100 mL) which
4. 4
   その他Some seeding material was prepared (

実験手順

A stirred solution of DDAIP base 4 (75 g, 263 mmol) in methanol (600 mL) was cooled to 0° C. then citric acid 8 (50.4 g, 0.263) 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 solvent was concentrated under vacuum. The residue was diluted with n-hexane (100 mL) which was not miscible with the product. Some seeding material was prepared (scratching the crude in a glass vial), and seeded to the crude to afford dodecyl 2-(dimethylamino)propanoate citrate salt (11, Nex-07) (120 g, yield: 95.6%) as a white solid, mp: 62-67° C. 1H-NMR (400 MHz, CDCl3): δ 0.85 (t, 3H), 1.3 (m, 18H), 1.5 (d, 3H), 1.7 (q, 2H), 2.7 (m, 2H), 2.9 (s, 6H), 4.1 (q, 1H), 4.2 (t, 2H); LCMS: 286 (M++1); HPLC: 88%.

出典