(4'-AMINO-BIPHENYL-4-YL)-CARBAMIC ACID TERT-BUTYL ESTER synthesis

Yield:206182-66-3 97%

Reaction Conditions:

with potassium carbonate in tetrahydrofuran;water;N,N-dimethyl-formamide at 20; for 5 h;

Steps:

103.1 Step 1: Synthesis of tert-butyl N-[4-(4-aminophenyl)phenyl]carbamate

Step 1: Synthesis of tert-butyl N-[4-(4-aminophenyl)phenyl]carbamate:H₂N- - <^^~^>- NHBoc[0705] To a stirred solution of 4-(4-aminophenyl)aniline (15.0 g, 81.42 mmol) in a mixed solvent of Ν,Ν-dimethylformamide / tetrahydrofuran /water (v/v/v = 100/300/50 mL) was added potassium carbonate (9.5 g, 68.74 mmol) and di-tert-butyl dicarbonate (13.67 g, 62.63 mmol) at rt. The resulting mixtire was stirred for 5h at rt. The reaction was then diluted by water (500 mL) and extracted with ethyl acetate (200 mL x 3). The organic layers were combined, washed with brine (50 mL x 2), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue which was purified by silica gel flash chromatography (eluent: ethyl acetate/petroleum ether, v:v = 1:2) to provide the titled product (yield: 97%) as a yellow solid.

References:

WO2016/118666,2016,A1 Location in patent:Paragraph 0704; 0705