Molbank 2007, M546 |
3-tert-butoxycarbonylamino-pyridine-2-carboxylic Acid
a Facult¨¦ des Sciences, Universit¨¦ Ibn
Zohr, BP 8061, 8000, Agadir,
Morocco
b Facult¨¦ Poly-disciplinaire de Safi, Universit¨¦
Cadi Ayyad, BP 4162, 46 000
c Laboratoire de Chimie Bioorganique & Analytique, FSTM, Universit¨¦
Hassan II -Mohammedia,BP 146, 20 800 Mohammedia, Morocco
Keywords: Saponification, Pyridopyrimidine, bioactivity
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¡ãC 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¡ãC (White powder from Ethyl acetate/petroleum ether)
IR
(KBr): 2994, 1727, 1677 cm-1
1H-NMR (300 MHz, DMSO-d6,
¦Ä, 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,
13C- NMR (75 MHz, DMSO-d6,
¦Ä, 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.
Acknowledgements
We
wish to thank the ministry ESRSFC of the Moroccan Government (PROTARS-P2T2/07)
for financial support.
© 2007 by MDPI (http://www.mdpi.org/). Reproduction is permitted for noncommercial purposes.