Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 93919-56-3, name is (4-(Trifluoromethoxy)phenyl)methanamine, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C8H8F3NO
General procedure: All purchased chemicals were used without further purification. All solvents were HPLC grade. Boc-Trp-OH (1.00 mmol) was dissolved in 10 mL of dioxane under nitrogen. Carbonyldiimidazole(1.02 mmol) was then added in a stepwise manner and the resulting mixture stirred for 3 h at room temperature and then heated to 50C for 30 min. The desired amine (1.03 mmol) was added to the reaction mixture at room temperature and stirring was continued for 48 h. The solvent was removed under reduced pressure and crude product was extracted with ethyl acetate (3 x 20 ml). The organic extracts were washed with 1M hydrochloric acid (15 mL), saturated sodium bicarbonate solution (15 mL) and water (15 mL), then dried over anhydrous MgSO4 and the solvent was removed under reduced pressure. To this crude compound in water (1 mL) was added anisole (2.00 mmol). The solution was then cooled to 0C prior to addition of trifluoroacetic acid (30.00 mmol) in 1 mL of water. After stirring for 1 h at 0C, the reaction mixture was allowed to warm to room temperature and stirring was continued for 12 h. The reaction mixture was then diluted with ethyl acetate (15 mL) and washed with saturated sodium bicarbonate solution (15 mL), water (15 mL) and brine solution (15 mL) and dried over anhydrous MgSO4. The solvent was removed under reduced pressure to afford the crude free amine which was directly used in the next step without further purification. To a solution of the above crude amine in dichloromethane (5 mL) was added carbonyldiimidazole (1.2 mmol) under nitrogen at room temperature. After 3 h stirring, morpholine or 1-Boc-piperazine (1.55 mmol) was added to the reaction mixture and stirred for another 12 h at room temperature. The solvent was removed under reduced pressure, diluted with ethyl acetate (15 mL) and washed with 1M hydrochloric acid (15 mL), saturated sodium bicarbonate solution (15 mL), brine solution (15 mL) and dried over anhydrous MgSO4. The crude product was then purified by preparative HPLC (Gradient 0 to 100% of 95/5 acetonitrile/water solution over 25 min) and freeze-dried. NMR spectral data of all synthesized compounds 1-10 are included in the supporting information (S1-S10 Figs). NMR spectra were recorded on Bruker Avance DRX-600 and Varian 400 MHz spectrometers at 298 K with TMS as internal standard. High-resolution mass spectrometry (HRMS) was performed on a Bruker micro-TOF by directin fusion in acetonitrile/H2O 70:30 at 3 muL/min using sodium formate clusters as an internal calibrant. Semi-preparative RP-HPLC purification of the compounds was performed using a Waters Delta 600 chromatography system fitted with a Waters 486 tuneable absorbance detector with detection at 214 nm. Purification was performed by eluting with solvents A (0.1% TFA in water) and B (9:1 CH3CN:H2O, 0.1% TFA) on a Vydac C18 250 x 22 mm (300 A) steel jacketed column at 20 mL/min. NH peak of Indole is not observed in some of the compounds in CDCl3 due to peak broadness.
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 93919-56-3.
Reference:
Article; Duprez, Wilko; Bachu, Prabhakar; Stoermer, Martin J.; Tay, Stephanie; McMahon, Roisin M.; Fairlie, David P.; Martin, Jennifer L.; PLoS ONE; vol. 10; 7; (2015);,
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