In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 147751-16-4 as follows. name: tert-Butyl methylsulfonylcarbamate
1.6 M n-Butyl lithium in hexanes (20.2 ml, 32.4 mmol) was added drop wise to a solution of N,N-diisopropylethylamine (5.91 ml, 33.9 mmol) in 25 ml dry THF in ice bath and stirred for 30 minutes. Then tert-butyl methylsulfonylcarbamate in 25 ml dry THF was added slowly and stirred at 0 C. for 1 hour. The mixture was then cooled to -78 C. and 4-phenoxy-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzaldehyde (3.01 g, 15.4 mmol) in 25 ml dry THF was added slowly. The reaction was slowly warmed up to room temperature and stirred at room temperature for 1 hour. Then it was quenched with water, acidified with 1N HCl to pH 3, extracted with ethyl acetate. The combined organic layer was then dried over Na2SO4, filtered and concentrated. Column purification gave 1 g product as off-white solid. 1H NMR (DMSO-d6, 300 MHz) delta ppm 11.34 (s, 1H), 9.39 (s, 1H), 7.54 (d, J=8.10 Hz, 1H), 7.42-7.37 (m, 2H), 7.28 (d, J=2.40, 1H), 7.22-7.12 (m, 2H), 7.03-7.01 (m, 2H), 5.43 (dd, J=9.3, 1.8 Hz, 1H), 4.01 (dd, J=13.5, 2.1 Hz, 1H), 3.54 (dd, J=14.7, 9.3 Hz, 1H), 1.42 (s, 9H). MS (ESI) m/z 418 [M-H]-.
According to the analysis of related databases, 147751-16-4, the application of this compound in the production field has become more and more popular.
Reference:
Patent; Anacor Pharmaceuticals, Inc.; GlaxoSmithKline; US2010/256092; (2010); A1;,
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