反应 #2286367

反应方程式

(±)-Alanine methyl ester hydrochloride salt

Et3N

nicotinoyl chloride

ethyl acetate

→

desired product

收率 69.0%

2-[(pyridine-3-carbonyl)-amino]-propionic acid methyl ester

收率 69.0%

溶剂

acetonitrile

brine

反应条件

后处理

1. 1
   workup.WAIT80° C. for 2 h
2. 2
   workup.ADDITIONThe reaction mixture was poured into a separatory funnel
3. 3
   其他The biphasic mixture was separated
4. 4
   洗涤the organic layer was washed one time with brine
5. 5
   干燥dried over MgSO4
6. 6
   过滤filtered
7. 7
   浓缩concentrated to dryness
8. 8
   其他The crude product was triturated in 80% ethyl acetate/hexanes overnight at ambient temperature
9. 9
   其他The solids were removed by filtration over Celite®
10. 10
    浓缩the filtrate was concentrated in vacuo

实验过程

(±)-Alanine methyl ester hydrochloride salt (35.2 g, 280 mmol) and Et3N (58.5 mL, 420 mmol) were sequentially added to a stirred solution of nicotinoyl chloride (19.8 g, 140 mmol) in acetonitrile (800 mL) and stirred at ambient temperature for 10 min and then 80° C. for 2 h. The reaction mixture was poured into a separatory funnel containing brine and ethyl acetate. The biphasic mixture was separated, and the organic layer was washed one time with brine, dried over MgSO4, filtered and concentrated to dryness. The crude product was triturated in 80% ethyl acetate/hexanes overnight at ambient temperature. The solids were removed by filtration over Celite® and the filtrate was concentrated in vacuo to give the desired product as a clear brown oil (20 g, 69%): 1H NMR (300 MHz, CDCl3) δ 9.04 (d, J=2.2 Hz, 1H), 8.75 (dd, J=4.9, 1.4 Hz, 1H), 8.13 (dt, J=7.7, 1.9 Hz, 1H), 7.40 (dd, J=8.0, 4.9 Hz, 1H), 6.92 (br s, 1H), 4.82 (m, 1H), 3.81 (s, 3H), 1.55 (d, J=7.1 Hz, 3H); ESIMS m/z 209 (M+1), m/z 207 (M−1).

来源