BENZYL 2-OXO-1,2-DIHYDROPYRIDIN-3-YLCARBAMATE Chemical Properties

Melting point:

175-178 °C

Boiling point:

474.3±45.0 °C(Predicted)

Density 

1.29±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

8.52±0.20(Predicted)

Appearance

Off-white to pink Solid

BENZYL 2-OXO-1,2-DIHYDROPYRIDIN-3-YLCARBAMATE Usage And Synthesis

Synthesis

At room temperature, 3-aminopyridin-2(1H)-one (3.25 g, 29.5 mmol) and sodium carbonate (6.26 g, 59.0 mmol) were dissolved in tetrahydrofuran (100 mL), and benzyl chloroformate (5.27 mL, 36.9 mmol) was added slowly and dropwise. The reaction mixture was stirred at room temperature for 24 hours. Upon completion of the reaction, the reaction mixture was diluted with ethyl acetate (150 mL) and filtered through Celite. The filtrate was concentrated under reduced pressure to about 200 mL and subsequently washed with water (40 mL) and dried with anhydrous magnesium sulfate. It was again concentrated under reduced pressure to about 50 mL and the precipitated white solid (first product) was collected by filtration. The remaining filtrate was concentrated to near dryness under reduced pressure and the residue was stirred with ether (50 mL) and the insoluble white solid (second batch of product) was collected by diafiltration. The two batches of products were combined and dried under vacuum at 50 °C to afford the target compound (2-oxo-1,2-dihydropyridin-3-yl)carbamic acid benzyl ester (5.77 g, 23.62 mmol, 80% yield) as a white solid.

References

[1] ChemMedChem, 2011, vol. 6, # 7, p. 1228 - 1237
[2] Patent: WO2007/27729, 2007, A1. Location in patent: Page/Page column 39-40
[3] Patent: WO2015/89143, 2015, A1. Location in patent: Page/Page column 83; 84
[4] Journal of Medicinal Chemistry, 1994, vol. 37, # 19, p. 3090 - 3099
[5] Patent: US2007/287696, 2007, A1. Location in patent: Page/Page column 33

BENZYL 2-OXO-1,2-DIHYDROPYRIDIN-3-YLCARBAMATE(147269-67-8)Related Product Information

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• 3-Benzyloxycarbonylamino-6-methyl-2-pyridone
• BENZYL (5-OXO-1,2,3,5-TETRAHYDROINDOLIZIN-6-YL)CARBAMATE
• 1-(T-BUTYLOXYCARBONYLMETHYL)-3-(BENZYLOXYCARBONYLAMINO)-2-PYRIDONE
• BENZYL 2-OXO-1,2-DIHYDROPYRIDIN-3-YLCARBAMATE