Open in another window 7. 1377 (OSO2); 1H NMR (400?MHz, CDCl3) 7.81C7.79 (m, 2H, Ar-H), 7.68C7.64 (m, 2H, Ar-H), 7.53C7.46 (m, 4H, Ar-H), 6.87 (d, 2H, NH, 174.8 (CO), 145.2, 137.4, 135.1, 134.3, 129.2 (2C), 128.5 (2C), 122.7 (2C), 120.7 (2C) [Ar-C], 46.4, 29.7 (2C), 29.6, 25.6 (2C), 25.5 [aliph. C]; LCCMS: 360.2 [M+ +1]. 4.3.5. 4-(Cyclohexanecarboxamido)phenyl 4-methylbenzenesulfonate (1e) Produce: 88%; mp: 171C4?C; IR (KBr disk, cm?1): 3740 E-7010 (NH), 2927, 2855 (CH stretching out), 1656 (CO), 1528, 1377 (OSO2); 1H NMR (400?MHz, CDCl3) 7.68 (d, 2H, Ar-H, 174.4 (CO), 145.4, 137.0, 132.2, 129.8 (2C), 128.6 (2C), 122.9 (2C), 120.5 (2C) [Ar-C], 46.5, 29.6 (2C), 25.6 (2C), 21.7, 14.1 [aliph. C]; LCCMS: 373.91 [M+ +1]. 4.3.6. 4-(Cyclohexanecarboxamido)phenyl 4-(tert-butyl)benzenesulfonate (1f) Produce: 85%; mp: 174C7?C; IR (KBr disk, cm?1): 3369 (NH), 2956, 2922, 2851 (CH stretching out), 1671 (CO), 1406, 1378 (OSO2); 1H NMR (400?MHz, CDCl3) 7.74 (d, 2H, Ar-H, 174.5 (CO), 145.4, 137.1, 132.2, 128.4 (2C), 126.2 (2C), 122.9 (2C), 120.5 (2C) [Ar-C], 46.5, 29.6 (2C), 25.6 (3C) [aliph. C]. LCCMS: 416.21 [M+ +1]. 4.3.7. 4-(Cyclohexanecarboxamido)phenyl 4-fluorobenzenesulfonate (1g) Produce: 87%; mp: 154C5?C; IR (KBr disk, cm?1): 3316 (NH), 2929, 2853 (CH stretching out), 1665 (CO), 1519, 1379 (OSO2); 1H NMR (400?MHz, CDCl3) 7.85C7.81(m, 2H, Ar-H), (d, 2H, Ar-H, 174.5 (CO), 145.2, 137.2, 131.5 (2C), 131.4, 122.9 (2C), 120.6, 116.7 (2C), 116.5 (2C) [Ar-C], 46.5, 29.6 (2C), 25.6 (3C) [aliph. C]; LCCMS: 378.23 [M+ +1]. 4.3.8. 4-(Cyclohexanecarboxamido)phenyl 4-(trifluoromethyl)benzenesulfonate (1h) Produce: 85%; mp: 171C2?C; IR (KBr disk, cm?1): 3327 (NH), 2931, 2850 (CH stretching out), 1661 (CO), 1407, 1386 (OSO2); 1H NMR (400?MHz, CDCl3) 7.96 (d, 2H, Ctnnb1 Ar-H, 174.6 (CO), 145.0, 138.8, 137.5, 136.0, 129.1 (2C), 126.4 (2C), 126.3, 122.7 (2C), 120.7 (2C) [Ar-C], 46.5, 29.6 (2C), 25.6 (3C) [aliph. C]; LCCMS: 427.94 [M+ +1]. 4.3.9. 4-(Cyclopentanecarboxamido)phenyl 4-methylbenzenesulfonate (1i) Produce: 80%; mp: 151C3?C; IR (KBr disk, cm?1): 3731 (NH), 2917, 2845 (CH stretching out), 1655 (CO), 1527, 1375 (OSO2); 1H NMR (400?MHz, CDCl3) 7.69 (d, 2H, Ar-H, 175.0 (CO), 145.5, E-7010 145.2, 137.3, 132.1, 129.8 (2C), 128.5 (2C), 122.8 (2C), 120.5 (2C) [Ar-C], 46.4, 30.5 (2C), 26.0 (2C), 21.7 [aliph. C]; LCCMS: 359.75 [M+ +1]. 4.4. Synthesis of the mark sulfamate substances 1jCm A remedy of substance 4a,b (0.456?mmol) in dry out DMF (10?mL) was cooled to 0?C, and NaH (60% dispersion in nutrient essential oil, 18.2?mg, 0.456?mmol) was added thereto under nitrogen atmosphere. A remedy of the correct sulfamoyl chloride (2.0?mmol) in dry out DMF (3?mL) was added dropwise towards the response mixture in the same heat. The response combination was stirred at space temperature immediately. After response completion, the combination was quenched with ethyl acetate (10?mL) and drinking water (10?mL). The organic coating was separated, as well as the aqueous coating was extracted with ethyl acetate (3??5?mL). The mixed organic coating extract were cleaned with saline (3??10?mL), and dried more than anhydrous sodium sulfate. The organic solvent E-7010 was evaporated under decreased pressure, and crude residue was purified by column chromatography (silica gel, suitable percentage of hexane/ethyl acetate) to get the pure item. 4.4.1. 4-(Cyclohexanecarboxamido)phenyl sulfamate (1j) Produce: 83%; mp: 174C6?C; IR (KBr disk, cm?1): 3393 (NH), 3299 (NH2), 2932, 2855 (CH stretching out), 1661 (CO), 1532, 1374 (OSO2); 1H NMR (400?MHz, CDCl3) 7.63 (d, 2H, Ar-H, 176.3 (CO), E-7010 146.5, 137.2, 122.3 (2C), 120.8 (2C) [Ar-C], 45.7, 29.3 (2C), 25.5, 25.4 (2C) [aliph. C]; LCCMs: 299.08 [M+ +1]. 4.4.2. 4-(Cyclohexanecarboxamido)phenyl methylsulfamate (1k) Produce: 90%; mp: 162C5?C; IR (KBr disk, cm?1): 3364 (NH), 3177 (NH), 2936, 2853 (CH stretching out), 1671 (CO), 1538, 1340 (OSO2); 1H NMR (400?MHz, CDCl3) 7.63 (d, 2H, Ar-H, 176.3 (CO), 146.2, 137.3, 122.8 (2C), E-7010 120.9(2C) [Ar-C], 45.7 (CH3), 29.3 (2C), 28.5, 25.5, 25.4 (2C) [aliph. C]; LCCMs: 312.99 [M+ +1]. 4.4.3..