Synthetic Route of 631-58-3, A common heterocyclic compound, 631-58-3, name is Propanethioamide, molecular formula is C3H7NS, its 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.
A mixture of propanethioamide ethyl] amino-i -oxo-3 -phenylpropane-2-ylcarbamate (12): A mixture of propanethioamide(69 mg, 0.78 mmol) and (5)-tert-butyl 4-bromo-i-(4-nitrophenyl)-3-oxobutan-2- ylcarbamate, 7, (0.300 g, 0.77 mmol) in CH3CN (4 mL) is refluxed for 2 hours. The reaction mixture is cooled to room temperature and diethyl ether is added to precipitate the intermediate 2-(nitrophenyl)-(5)- 1 -(4-ethylthiazol-2-yl)ethylamine which is isolated by filtration as the hydrobromide salt. The hydrobromide salt is dissolved in DMF (8mL) together with diisoproylethylamine (0.38 mL, 2.13 mmol), i-hydroxybenzotriazole (107 mg, 0.71 mmol) and (5)-(2-methoxycarbonyl-amino)-3-phenylpropionic acid (175 mg, 0.78 mmol). The mixture is stirred at 0 C for 30 minutes then at room temperature overnight. The reaction mixture is diluted with water and extracted with EtOAc. The combined organic phase is washed with 1 N aqueous HC1, 5 % aqueous NaHCO3, water and brine, and dried over Na2SO4. The solvent is removed in vacuo to afford 0.300g (81% yield) of the desired product which is used without further purification. LC/MSESI+MS 483 (M+1).
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; AERPIO THERAPEUTICS INC.; PETERS, Kevin; SHALWITZ, Robert; JANUSZ, John; SMITH, Alexander; WO2014/145068; (2014); A1;,
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