Ethanol → 3-Pyridinepropanoic acid, β-amino-, ethyl ester, hydrochloride (1:1)
Reaction equation
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]Participants
Procedure
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 termperature 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) δ 9.32 (br s, 3 H), 9.21 (br s, 1 H), 8.87-8.95 (m, 2 H), 8.09-8.14 (m, 1 H), 4.93 (br s, 1 H), 3.90-4.15 (m, 2 H), 3.20-3.38 (m, 2 H), 1.11 (t, 3 H, J=7 Hz); 13C NMR (DMSO-d6) δ 168.8, 144.5, 142.8, 142.6, 136.2, 126.7, 60.7, 47.9, 37.2, 13.9.
Workup
- customat 0° C.
- temperaturerefluxed for 3 hours
- temperatureAfter 2 hours at reflux all of the solid
- dissolutionhad dissolved
- temperatureto cool to room termperature
- filtrationThe slurry was filtered
- washthe solid was washed with copious amounts of ethanol
- customThe solid was dried in vacuo (60° C., <1 mm)
Sources & evidence
- ORD record
- ord-18bd34f2833145179d36f942e355a3b1
- Source dataset
- uspto-grants-1999_03
- Patent number
- US05877200
Reaction notes
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