| Identification | Back Directory | [Name]
2-Oxopiperidine-4-carboxy... | [CAS]
24537-50-6 | [Synonyms]
2-Oxopiperidine-4-carboxy...
2-Oxopiperidine-4-carboxylic acid
4-Piperidinecarboxylic acid, 2-oxo- | [Molecular Formula]
C6H9NO3 | [MDL Number]
MFCD13659408 | [MOL File]
24537-50-6.mol | [Molecular Weight]
143.14 |
| Chemical Properties | Back Directory | [Boiling point ]
437.0±38.0 °C(Predicted) | [density ]
1.286±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
4.62±0.20(Predicted) | [Appearance]
White to off-white Solid |
| Hazard Information | Back Directory | [Uses]
2-Oxopiperidine-4-carboxylic Acid can be synthesized from 2-Hydroxyisonicitonic Acid (H942895), a compound used in the synthesis of selective inhibitors of neuropeptide Y Y5 inhibiting food intake. 2-Hydroxyisonicitonic Acid is also used in the optimization of p-subsite residues of HIV protease inhibitors. | [Synthesis]
Under nitrogen atmosphere, 2-hydroxyisonicotinic acid (500 g, 3.59 mol) was dissolved in methanol (10 L) and palladium hydroxide (150 g) was added to a 20 L autoclave. The reaction mixture was stirred at room temperature and 5 kg/cm2 hydrogen pressure for 18 hours. After confirming complete consumption of the feedstock by LCMS monitoring, the reaction mixture was filtered through a diatomaceous earth pad and the filtrate was concentrated under reduced pressure. The resulting residue was ground with ether (2.5 L) and dried under vacuum to afford 2-oxopiperidine-4-carboxylic acid (450 g, 85% yield) as an off-white solid.1H NMR (500 MHz, DMSO-d6): δ 12.37 (s, 1H), 7.44 (s, 1H), 3.16-3.12 (m, 2H), 2.78-2.71 (m, 1H), 2.33-2.71 (m, 1H), 2.33-2.71 (m, 1H). 1H), 2.33-2.21 (m, 2H), 1.98-1.92 (m, 1H), 1.74-1.63 (m, 1H). LCMS (m/z): 144.2 [M++1]. | [References]
[1] European Journal of Organic Chemistry, 2018, vol. 2018, # 46, p. 6486 - 6493
[2] Patent: WO2018/26798, 2018, A1. Location in patent: Page/Page column 33; 34
[3] Patent: US2007/191406, 2007, A1. Location in patent: Page/Page column 27 |
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