2-TERT-BUTOXYCARBONYLAMINO-5-NITRO-BENZOIC ACID METHYL ESTER synthesis
- Product Name:2-TERT-BUTOXYCARBONYLAMINO-5-NITRO-BENZOIC ACID METHYL ESTER
- CAS Number:147290-58-2
- Molecular formula:C13H16N2O6
- Molecular Weight:296.28
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Yield:147290-58-2 90%
Reaction Conditions:
with dmap;triethylamine in tetrahydrofuran at 20; for 4 h;Inert atmosphere;
Steps:
2.1.1. Methyl 2-[(tert-butoxycarbonyl)amino]-5-nitrobenzoate (8).
A solution of methyl 5-nitroanthranilate (7) (10 g, 51 mmol), di-tert-butylcarbonate (Boc2O, 22.3 g, 102 mmol, 2.0equiv), DMAP (0.623 g, 5.1 mmol, 0.1 equiv) and triethylamine (6.90 mL, 51.1 mmol, 1.0equiv) in dry THF (500 mL) was stirred at room temperature for 4 h. Evaporation of thesolvent gave a crude mixture which was purified by chromatography on silica gel withdichloromethane/petroleum ether (0:100 to 50:50, v/v) as eluent to give 8 (13.6 g, 90%) as apale yellow powder: mp = 150-152 °C; IR (cm-1) max 3219, 3120, 3103, 2970, 2931, 1741,1696 , 1586, 1508, 1242, 1148, 1049, 965, 844, 744; 1H NMR (300 MHz, DMSO-d6) δ 10.50(s, 1H, NHBoc), 8.67 (d, J = 2.3 Hz, 1H, H6), 8.45 (dd, J = 9.3, 2.5 Hz, 1H, H4), 8.40 (d, J =9.3 Hz, 1H, H3), 3.92 (s, 3H, OCH3), 1.50 (s, 9H, 3 × CH3); 13C NMR (75 MHz, DMSO-d6) δ166.5, 151.5, 146.3, 140.6, 129.2, 126.3, 118.9, 115.1, 81.7, 53.1, 27.8 (3C); HRMS calcd forC13H15N2O6 [M-H]- 295.0930 found 295.0924.
References:
Hédou, Damien;Harari, Marine;Godeau, Julien;Dubouilh-Benard, Carole;Fruit, Corinne;Besson, Thierry [Tetrahedron Letters,2015,vol. 56,# 27,art. no. 46290,p. 4088 - 4092] Location in patent:supporting information
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