Uses
(R)-tert-Butyl (1-(3-Bromophenyl)ethyl)carbamate is used as a reactant in the synthesis of macrocyclic peptidomimetic inhibitors of flaviviridae viruses.
Synthesis
General procedure for the synthesis of tert-butyl (R)-1-(3-bromophenyl)ethylcarbamate from di-tert-butyl dicarbonate and (R)-1-(3-bromophenyl)ethylamine: In Example 16, Compound 16a was synthesized as follows: (R)-1-(3-bromophenyl)ethylamine (1.023 g, 5.112 mmol) was dissolved in dichloromethane (20 mL), followed by addition of triethylamine (720 μL, 5.112 mmol) and di-tert-butyl dicarbonate (1.784 g, 8.179 mmol). The reaction mixture was stirred at room temperature overnight. Upon completion of the reaction, the volatile solvent was removed by distillation under reduced pressure and the residue was purified by silica gel column chromatography using a 50 g Isolute column eluting with a continuous gradient of hexane/Et2O (1:0 to 4:1) to afford the title compound tert-butyl (R)-1-(3-bromophenyl)ethylcarbamate (1.552 g, 100%) as a white solid.1H NMR ( 300MHz, CDCl3) δ 1.43 (br s, 12H), 4.77 (br s, 2H), 7.16-7.26 (m, 2H), 7.39 (dt, J = 2.0,7.1Hz, 1H), 7.46 (s, 1H).
References
[1] Patent: WO2012/78915, 2012, A1. Location in patent: Page/Page column 90
[2] Patent: WO2013/48942, 2013, A1. Location in patent: Paragraph 00198
[3] Patent: WO2013/151923, 2013, A1. Location in patent: Paragraph 00186
[4] Patent: WO2013/185093, 2013, A1. Location in patent: Page/Page column 61; 62
[5] Patent: WO2013/185103, 2013, A1. Location in patent: Page/Page column 63
