تفاعل #2286367

معادلة التفاعل

(±)-Alanine methyl ester hydrochloride salt

Et3N

nicotinoyl chloride

ethyl acetate

→

desired product

المردود 69.0%

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

المردود 69.0%

المذيبات

acetonitrile

brine

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

(±)-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).

المصدر