Ethanol → Ethyl 3-amino-3-(3-pyridyl)propionate hydrochloride

反応式

S(Cl)([Cl:3])=O.[NH2:5][CH:6]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:7][C:8]([OH:10])=[O:9].[CH2:17](O)[CH3:18]>>[ClH:3].[NH2:5][CH:6]([C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1)[CH2:7][C:8]([O:10][CH2:17][CH3:18])=[O:9]

参加物

反応物 3

HCID 702Ethanol

HCID 24386Thionyl Chloride

HCID 36065473-Amino-3-(pyridin-3-yl)propanoic acid

生成物 1

HCID 18323069Ethyl 3-amino-3-(3-pyridyl)propionate hydrochloride収率 79%

実験手順

To 40 mL of stirred ethanol at 0° C. under nitrogen was slowly added thionyl chloride (3.3 mL, 45 mmol) followed by addition of 3-amino-3-(3-pyridyl)propionic acid (2.65 g, 15 mmol). The reaction mixture was allowed to slowly warm to room temperature and then refluxed for 3 hours. After 2 hours at reflux all of the solid had dissolved. The reaction mixture was allowed to cool to room temperature and stirred overnight. The slurry was filtered and the solid was washed with copious amounts of ethanol. The solid was dried in vacuo (60° C., <1 mm) to afford 3.17 g (79%) of ethyl 3-amino-3-(3-pyridyl)propionate hydrochloride as a white powder: 1H NMR (DMSO-d6, 250 MHz) δ9.32 (br s, 3 H), 9.21 (br s, 1H), 8.87-8.95 (m, 2H), 8.09-8.14 (m, 1H), 4.93 (br s, 1H), 3.90-4.15 (m, 2H), 3.20-3.38 (m, 2H), 1.11 (t, 3H, J=7 Hz); 13C NMR (DMSO-d6) δ168.8, 144.5, 142.8, 142.6, 136.2, 126.7, 60.7, 47.9, 37.2, 13.9.