Synthetic Route of 147291-66-5, A common heterocyclic compound, 147291-66-5, name is tert-Butyl 3-aminobenzylcarbamate, molecular formula is C12H18N2O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
The solution of EDCI (3.14g, 16.38mmol) and DMAP (100mg, 0.82mmol) in 10mL DCM was added dropwise to a mixture of tert-butyl-3-aminobenzyl-carbamate (2.0g, 9.01mmol) and benzoic acid (1.0g, 8.19mmol) in 20mL DCM at 0C under nitrogen atmosphere, and the mixture was warmed to r.t. and stirred overnight. After quenched with water and extracted with DCM, the organic layer was washed with 1M NaOH (20mL), 1M HCl (20mL), and saturated NaHCO3 (10mL), dried over Na2SO4, and concentrated under reduced pressure. The Boc-protected 12a was dissolved in DCM (5mL), trifluoroacetic acid (5mL) was added. The reaction mixture was allowed to stir for 2hat r.t. and concentrated under reduced pressure. The residue was purified by column chromatography over silica gel and further purified by recrystallization (ethyl ether) to obtain the title compound as a white solid (1.2g, yield 64.8%). 1H NMR (600MHz, DMSO-d6) delta: 10.42 (1H, s), 8.34 (3H, s), 8.01-7.96 (3H, m), 7.70 (1H, d, J=8.4Hz), 7.61 (1H, t, J=8.4Hz), 7.54 (2H, t, J=7.8Hz), 7.41 (1H, t, J=7.8Hz), 7.22 (1H, d, J=7.8Hz), 4.04 (2H, s). 13C NMR (150MHz, DMSO-d6) delta: 166.1, 139.9, 135.2, 134.9, 132.1, 129.4, 128.8, 128.1, 124.4, 121.3, 121.0, 42.9.
The synthetic route of 147291-66-5 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Zhao, Yaxue; Wang, Zhongli; Zhang, Jianchen; Zhou, Huchen; European Journal of Medicinal Chemistry; vol. 122; (2016); p. 178 – 184;,
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