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ETHYL 6-(BIS-TERT-BUTOXYCARBONYL)AMINONICOTINAT synthesis

2synthesis methods
39658-41-8 Synthesis
Ethyl 6-aminonicotinate

39658-41-8
131 suppliers
$6.00/250mg

24424-99-5 Synthesis
Di-tert-butyl dicarbonate

24424-99-5
813 suppliers
$13.50/25G

ETHYL 6-(BIS-TERT-BUTOXYCARBONYL)AMINONICOTINAT

1089330-72-2
6 suppliers
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Yield:1089330-72-2 85%

Reaction Conditions:

with dmap in acetone;tert-butyl alcohol at 20;

Steps:

140.2 Synthesis of ethyl 6-[bis(tert-butoxycarbonyl)amino]nicotinate:

To a solution of ethyl 6-aminonicotinate (160.0 g, 963 mmol) in t-BuOH (1.7 L) and acetone (560 mL) was added DMAP (2.38 g, 19.1 mmol) and di-t-butyl dicarbonate (420.0 g, 1.92 mol). The reaction was stirred at room temp overnight. The solvent was removed and hexane/dichloromethane (2.5 L, 3:1) was added. The mixture was cooled to -20 °C for 2 h. The solid was collected by filtration and dried in vacuo to give ethyl 6-[bis(tert-butoxycarbonyl)amino]nicotinate (300.0 g, 85 % yield)

References:

WO2013/59587,2013,A1 Location in patent:Page/Page column 206; 207