Application of 154350-29-5,Some common heterocyclic compound, 154350-29-5, name is Cyclopropanesulfonamide, molecular formula is C3H7NO2S, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To a solution of (22E)-3-oxo-4,6,22-cholatrien-24-oic acid (2.00 g, 5.43 mmol) in CH2CI2(40 mL) was added EDCI (1.69 g, 10.9 mmol) and DMAP (1.33 g, 10.9 mmol).Cyclopropane sulfonamide (1.97 g, 16.3 mmol) was added and the reaction was stirred at room temperature for 22 h. Water (25 mL) was added and the layers were separated. The aqueous layer was extracted with CH2CI2 (2 x 25 mL) and the combined organics were washed with 2 M aq HCI (20 mL), 10percent aq. NaCI (10 mL), dried over sodium sulfate andconcentrated under reduced pressure. The residue was purified by column chromatography on silica gel (0-10percent acetone in toluene) to give the desired product (1.68 g, 66percent) asan off-white solid. OH (400 MHz, CDCI3); 8.90 (1H, s, NH), 6.95 (1H, dd, J15.5,9.0, 023-OH), 6.11 (2H, brs, 06-OH and 07-OH), 5.86 (1H, dd, J15.5, 0.5, 022-OH), 5.68 (1H, s, 04-OH), 3.00 (1H, dddd, J 12.8, 9.5, 8.1, 4.8, SO2OH), 2.64 (1H, ddd, J 18.1, 14.4,5.4, O2OHaHb), 2.51-2.41 (1H, m, 02-OHaHb), 2.40-2.28 (1H, m), 2.25-2.15 (1H, m), 2.09-1.96 (2H, m), 1.85-1.64 (3H, m), 1.63-1.52 (1H, m), 1.51-1.17 (9H, m), 1.17-1.07 (5H, m),1.12 (3H, s, 019-OH3), 0.80 (3H, s, 018-OH3); 00 (100 MHz, 0D013); 200.0, 164.2, 164.1,155.5, 141.3, 127.9, 123.6, 119.4,54.7, 53.2, 50.6, 43.8, 39.8, 39.3, 37.8, 36.1, 33.9, 33.9,31.5, 28.1, 23.7, 20.6, 19.1, 16.3, 12.2, 6.3, 6.3.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Cyclopropanesulfonamide, its application will become more common.
Reference:
Patent; NZP UK LIMITED; WEYMOUTH-WILSON, Alexander Charles; KOMSTA, Zofia; WALLIS, Laura; EVANS, Timothy; (139 pag.)WO2017/199036; (2017); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics