154350-29-5, name is Cyclopropanesulfonamide, belongs to amides-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. COA of Formula: C3H7NO2S
29.8 g (246 mmol) of cyclopropanesulfonamide, 4.82 g (11.4 mmol) of tert-butyl XPhos, 1.38 g (3.77 mmol) of bis(eta3-allyl-mu-chloropalladium), and 36.6 g (265 mmol) of potassium carbonate were added sequentially to a solution of 69.3 g (189 mmol) of (1R,5S,6r)-tert-butyl 6-(3-bromophenyl)-6-ethyl-3-azabicyclo[3.1.0]hexane-3-carboxylate, which was obtained in Reference Example 3-(b), in 400 mL of toluene with stirring under an argon stream, and the mixture was stirred at room temperature for 10 minutes, and was then stirred for 1.5 hours while heated at 110¡ã C. The obtained reaction solution was filtered through Celite, the Celite was washed with toluene, and the filtrate was concentrated under a reduced pressure. Then, 300 mL of tert-butyl methyl ether and 300 mL of a 1 N aqueous sodium hydroxide solution were added to the obtained residue to obtain an aqueous layer by liquid separation. Then, 160 mL of 2 N hydrochloric acid and 300 mL of tert-butyl methyl ether were added to the obtained aqueous layer to obtain an organic layer by liquid separation. The organic layer was washed with a saturated aqueous sodium chloride solution, dried with anhydrous magnesium sulfate, and concentrated under a reduced pressure. Then, 200 mL of hexane and 22 mL of ethyl acetate were added to the obtained residue, and the mixture was stirred at room temperature for 30 minutes and then stirred with ice cooling for 10 minutes. The precipitated solid was collected by filtration and dried at 50¡ã C. under a reduced pressure to obtain 54.4 g of the titled compound as a white solid. (Yield 70percent) Mass spectrum (CI, m/z): 407[M++1] 1H-NMR spectrum (400 MHz, CDCl3) deltappm: 7.26 (dd, J=7.8, 7.8 Hz, 1H), 7.16 (dd, J=1.9, 1.9 Hz, 1H), 7.11-7.05 (m, 2H), 6.34 (s, 1H), 3.65 (dd, J=5.3, 11.4 Hz, 1H), 3.60 (dd, J=5.3, 11.5 Hz, 1H), 3.54 (d, J=11.4 Hz, 1H), 3.48 (d, J=11.5 Hz, 1H), 2.46 (tt, J=4.8, 8.0 Hz, 1H), 1.90 (dd, J=8.0, 5.2 Hz, 1H), 1.89 (dd, J=8.0, 5.2 Hz, 1H), 1.64-1.53 (m, 2H), 1.47 (s, 9H), 1.20-1.12 (m, 2H), 1.00-0.93 (m, 2H), 0.82 (t, J=7.4 Hz, 3H)
The synthetic route of 154350-29-5 has been constantly updated, and we look forward to future research findings.
Reference:
Patent; SANWA KAGAKU KENKYUSHO CO., LTD.; UBE INDUSTRIES, LTD.; Iwamura, Ryo; Tsuzaki, Yasunori; Setoguchi, Hiroyuki; Akaza, Hiroto; Yamamoto, Yasuhito; Takama, Akira; Kuno, Yuka; (53 pag.)US2018/148409; (2018); A1;,
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