Carbamic acid, N-[1-methyl-1-(3-nitrophenyl)ethyl]-, 1,1-dimethylethyl ester synthesis
- Product Name:Carbamic acid, N-[1-methyl-1-(3-nitrophenyl)ethyl]-, 1,1-dimethylethyl ester
- CAS Number:180081-52-1
- Molecular formula:C14H20N2O4
- Molecular Weight:280.32
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Yield:180081-52-1 86%
Reaction Conditions:
with sodium hydrogencarbonate in tetrahydrofuran;water at 0 - 20; for 16 h;
Steps:
tert-Butyl (2-(3-nitrophenyl)propan-2-yl)carbamate (9)
To a solution of 8 (16.9 mg, 0.09 mmol) in anhydrous THF (0.7 mL), and saturated aqueous NaHCO3 (0.7 mL) was added di-tert-butyl dicarbonate (0.06 mL, 0.28 mmol) at 0 °C. The mixture was allowed to rise to room temperature, and stirred for 16 h. After being quenched by the addition of saturated ammonium chloride solution, the reaction was extracted with EtOAc (2 × 15 mL). The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated. The residue was purified by column chromatography on silica gel (EtOAc/hexane, 10:90) to afford 9 (23.7 mg, 86%) as a white solid; 1H NMR (CDCl3, 500 MHz) 8.26 (1 H, t, J = 2.3 Hz), 8.08 (1 H, d, J = 8.0 Hz), 7.73 (1 H, d, J = 7.4 Hz), 7.49 (1 H, t, J = 8.0 Hz), 5.08 (1 H, br), 1.64 (9 H, s), 1.39 (6 H, s); 13C NMR (CDCl3, 125 MHz) 154.0, 149.6, 148.3, 131.1, 129.2, 121.5, 120.0, 79.7, 54.7, 29.6, 28.3.
References:
Suebsuwong, Chalada;Pinkas, Daniel M.;Ray, Soumya S.;Bufton, Joshua C.;Dai, Bing;Bullock, Alex N.;Degterev, Alexei;Cuny, Gregory D. [Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,# 4,p. 577 - 583] Location in patent:supporting information
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