Nesulfonamide (170 mmol, 1.00 eq.) was dissolved in 250 mL acetonitrile. Towards the homogeneous resolution 50 mL acetic anhydride (54 g, 529 mmol, three.11 eq.) and 300 mL concentrated sulfuric acid (0.55 g/5.60 mmol/3 mol ) was added. The reaction mixture was heated to 60 C for 3 h after which permitted to cool to space temperature overnight while stirring. The solvent was removed below reduced stress, plus the residue dissolved in 150 mL water with each other with 20 mL brine. The aqueous remedy was continuously extracted with methylene chloride more than three days employing a Kutscher teudel extractor. The methylene chloride was then removed beneath decreased stress. 300 mL toluene was added to the residue, along with the mixture cooled to 4 C overnight. The toluene was decanted meticulously and replaced by 300 mL of fresh toluene, repeating the process. The raw item was sublimed in higher vacuum using a bath temperature of 30 C, using a cold nger cooled with dry ice. 8.16 g of your title compound (43 mmol/25 yield) were obtained as colourless solid. Sublimation needs to be slow and at or under 30 C, to avoid co-sublimation of triuoromethanesulfonamide, the absence of which was conrmed by 19F and 13C NMR. 1 H NMR (CD3CN, 400 MHz, d in ppm): 9.CD79B Protein Source 93 (br s, 1H, NH), 2.16 (s, 3H, COCH3). 13 C1H NMR (CD3CN, 100 MHz, d in ppm): 168.64 (s, COCH3), 120.27 (q, 1JC/F 320.7 Hz, CF3), 24.47 (s, COCH3). 19 1 F H NMR (CD3CN, 377 MHz, d in ppm): 7.78 (s, SO2CF3). HRMS, ESI m/z discovered 189.9792, calc. 189.9786 (M H) Sodium acetyl(triuoromethylsulfonyl)imide [Na] [N(Tf)(Ac)]. 5.80 g N-((triuoromethyl)sulfonyl)acetamide (30.four mmol/1.00 eq.) was dissolved at 0 C in 25 mL of water. This option was slowly neutralised with 2.58 g sodium bicarbonate (30.7 mmol/1.01 eq.). The resulting homogeneous resolution was frozen in liquid nitrogen and allowed to thaw under high6408 | Chem. Sci., 2020, 11, 6405This journal is the Royal Society of ChemistryEdge Post H NMR (CD3CN, 400 MHz, d in ppm): 10.42 (br s, 1H, NH), 3.32 (s, 3H, SO2CH3). 13 C1H NMR (CD3CN, one hundred MHz, d in ppm): 156.76 (q, 2JC/F 41.1 Hz, COCF3), 115.75 (q, 1JC/F 287.8 Hz, COCF3), 42.04 (s, SO2CH3). 19 1 F H NMR (CD3CN, 377 MHz, d in ppm): 6.29 (s, COCF3). HRMS, ESI m/z identified 189.9791, calc. 189.9786 (M H) Sodium (methanesulfonyl)(2,two,2-triuoroacetyl)imide [Na] [N(Ms)(TFA)]. 7.56 g two,two,2-triuoro-N-(methylsulfonyl)acetamide (39.6 mmol/1.00 eq.) was dissolved at 0 C in 25 mL of water. The resolution was gradually neutralised with three.32 g sodium bicarbonate (39.five mmol/1.00 eq.). The resulting homogeneous solution was frozen in liquid nitrogen and allowed to thaw under high vacuum.Annexin A2/ANXA2 Protein Biological Activity The resulting solid was dried under high vacuum to continuous mass, giving 8.PMID:34235739 five g from the title compound (39.eight mmol/quantitative yield) as a colourless solid. 1 H NMR (D2O, 400 MHz, d in ppm): three.14 (s, SO2CH3). 13 C1H NMR (D2O, 100 MHz, d in ppm): 163.98 (q, 2JC/F 36.1 Hz, COCF3), 116.68 (q, 1JC/F 287.two Hz, COCF3), 39.45 (s, SO2CH3). 19 1 F H NMR (D2O, 377 MHz, d in ppm): five.66 (s, COCF3). 1-Butyl-3-methylimidazolium (methylsulfonyl)(two,2,2triuoroacetyl)imide [C4C1im][N(Ms)(TFA)]. 5.76 g 1-butyl-3methylimidazolium chloride (33.0 mmol/1.00 eq.), eight.five g NaN(Ms)(TFA) (39.eight mmol/1.21 eq.), 250 mL methylene chloride, and 20 mL water were stirred together for 1 h. The organic phase was separated and washed three times with every single 20 mL water. No halide was discovered when testing the last washing water with aqueous silver nitrate option. The organic phase was dried more than molecul.