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Short Note

3-tert-butoxycarbonylamino-pyridine-2-carboxylic Acid

1
Faculté des Sciences, Université Ibn Zohr, BP 8061, 8000, Agadir, Morocco
2
Faculté Poly-disciplinaire de Safi, Université Cadi Ayyad, BP 4162, 46 000 Safi, Marocco
3
Laboratoire de Chimie Bioorganique & Analytique, FSTM, Université Hassan II -Mohammedia,BP 146, 20 800 Mohammedia, Morocco
*
Author to whom correspondence should be addressed.
Molbank 2007, 2007(3), M546; https://doi.org/10.3390/M546
Submission received: 23 January 2006 / Accepted: 24 February 2006 / Published: 30 March 2007
Molbank 2007 m546 i001
To the carbamic acid tert-butylester 1 (1.03 g, 4.08 mmol) in methanol (15 ml) was added 1.4 equivalents of NaOH (2N). The mixture was stirred at 50-60°C for 6 hours. After cooling to room temperature, the solvent was removed under reduce pressure. The residue was dissolved in water and acidified with HCl (15%) to pH 2 and extracted with dichloromethane (3 x 15 ml). The organic layer fractions were combined, dried (MgSO4) and the solvent was evaporated in vacuum to give a white solid 2 (0.924 g, 95%).
Mp 154°C (White powder from Ethyl acetate/petroleum ether)
IR (KBr): 2994, 1727, 1677 cm-1
1H-NMR (300 MHz, DMSO-d6, δ, ppm): 1.48 (s, 9H, CH3), 7.69 (dd, 1H, J = 8.5, 4.5 Hz, H-5), 8.31 (dd, 1H, J = 4.5, 1.3 Hz, H-4), 8.75 (dd, 1H, J = 8.5, 1.3 Hz, H-6), 10.79 (s, 1H, NH).
13C- NMR (75 MHz, DMSO-d6, δ, ppm): 27.82 (3CH3), 80.85 (C(CH3)3), 127.80, 128.31, 132.13, 138.75, 140.25, 152.00, 167.04.
MS m/z: 239 [M+1], 183, 165, 147, 139, 121
Elemental analysis: Calculated C11H14l N2O4: C, 55.46; H, 5.92; N, 11.76 Found: C, 55.36; H, 5.86; N, 11.79.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

We wish to thank the ministry ESRSFC of the Moroccan Government (PROTARS-P2T2/07) for financial support.

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MDPI and ACS Style

Mamouni, R.; El Haddad, M.; Akssira, M. 3-tert-butoxycarbonylamino-pyridine-2-carboxylic Acid. Molbank 2007, 2007, M546. https://doi.org/10.3390/M546

AMA Style

Mamouni R, El Haddad M, Akssira M. 3-tert-butoxycarbonylamino-pyridine-2-carboxylic Acid. Molbank. 2007; 2007(3):M546. https://doi.org/10.3390/M546

Chicago/Turabian Style

Mamouni, Rachid, Mohammadine El Haddad, and Mohamed Akssira. 2007. "3-tert-butoxycarbonylamino-pyridine-2-carboxylic Acid" Molbank 2007, no. 3: M546. https://doi.org/10.3390/M546

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