Introduction of a new synthetic route about 1,1-Dioxo-isothiazolidine

With the rapid development of chemical substances, we look forward to future research findings about 5908-62-3

1,1-Dioxo-isothiazolidine, cas is 5908-62-3, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

5908-62-3, Scheme 13d5-Hydroxy-4-(7-iodo- 1 , 1 -dioxo- 1 ,4-dihydro- 1 lambda6-benzo[ 1 ,2,4]thiadiazin-3-yl)-2-(3- methyl-butyl)-6-1hiophen-2-yl-2H-pyridazin-3-one (3a); (0.25 g, 0.438 mmol), potassium triphosphate (0.465 g, 2.19 mmol), sarcosine (0.023 g, 0.263 mmol), and copper (I) iodide (0.021 g, 0.110 mmol) were combined. Anhydrous N1N- dimethylformamide (3 mL) was added followed by isothiazolidine 1,1-dioxide (0.531 g, 4.38 mmol, prepared according to the procedure from Org. Lett; 5; 22; 2003; 4175- 4178). The solution was degassed while stirring under vacuum and the flask charged with nitrogen. The mixture stirred at 1000C for 16 h. LC-MS indicated the major product to be the amino acid intermediate. Additional isothiazolidine 1,1-dioxide (0.531 g, 4.38 mmol) was added. The solution was degassed while stirring under vacuum and the flask charged with nitrogen. The mixture stirred at 1000C for 16 h. LC-MS indicated complete reaction at this point.Upon cooling, the mixture was diluted with ethyl acetate (80 mL), washed with IM aqueous hydrochloric acid (2 x 10 mL), saturated aqueous ammonium chloride (10 mL), dried over magnesium sulfate filtered. Methyl alcohol (100 mL) was added and the desired product crystallized over a period of 2 h. Collection by filtration followed by rinsing with methyl alcohol (2 x 10 mL) followed by drying in vacuo for 3 h afforded the desired product, 4-[7-(l,l-dioxo-llambda6-isothiazolidm-2-yi)-l,l-dioxo-l,4- dihydro-llambda6-benzo[l,2,4]miadiazin-3-yl]-5-hydroxy-2-(3-methyl-butyl)-6-thiophen- 2-yl-2H-pyridazin-3-one (66a) (0.0693, 0.123 mmol, 28 % yield), as an orange powder. 1H NMR (400 MHz, DMSO-d6) delta: 0.96 (6H, d, J= 6.2 Hz), 1.59 – 1.71 (3H, m), 2.44 (2H, quintet, J= 7.1 Hz), 3.59 (2H, t, J= 6.9 Hz), 3.85 (2H, t, J= 6.7 Hz), 4.17 (2H, t, J= 6.7 Hz), 7.17 (IH, dd, J1 = 5.6 Hz, J2 = 3.9 Hz), 7.54 – 7.58 (2H, m), 7.68 – 7.71 (2H, m), 7.91 (IH, d, J= 4.0 Hz), 13.94 (IH, s). LC-MS (ESI): (exact mass: 563.10): m/e = 564.66 [M+H]+ (100 %).

With the rapid development of chemical substances, we look forward to future research findings about 5908-62-3

Reference£º
Patent; ANADYS PHARMACEUTICALS, INC.; WO2008/82725; (2008); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com