反応 #2286367

反応方程式

(±)-Alanine methyl ester hydrochloride salt

Et3N

nicotinoyl chloride

ethyl acetate

→

desired product

収率 69.0%

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

収率 69.0%

溶媒

acetonitrile

brine

反応条件

後処理

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

実験手順

(±)-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).

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