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
Intermediate 4 (0.146 g, 0.150 mmol) and isothiazolidine 1,1-dioxide (0.181 g, 1.496 mmol) were dissolved into anhydrous acetonitrile (1.5 mE). para-Toluenesulfonic acid monohydrate (2.84 mg, 0.015 mmol) was added in one portion. The reaction mixture was stirred at room temperature for two hours.10479] Aqueous saturated NaHCO3 was added. The mixture was extracted several times with ethyl acetate. The organic extracts were combined, dried over Na2SO, decanted and concentrated to give a colorless tar crude product.10480] The crude product was dissolved in MeOH (2.5 mE) and was purified in one injection via preparative-scale reverse phase chromatography (40-90% acetonitrile-water plus 0.1% TFA modifier on 100 g C18 ISCO column).10481] The first eluting peak fractions were pooled and reduced to about volume on a rotary evaporatot The remaining solution was made basic with saturated aqueous NaHCO4 and was extracted several times with EtOAc. The organic extracts were combined, dried over Na SO4, decanted and concentrated to give Example 14 (0.05 g, 0.044 mmol, 29.3% yield) as a white solid.Example 1410482] ESIMS [M+NH4] 1082.8, [M-H] 1063.7.10483] HRMS: calculated for C55H89N2O14PSNa as sodium adduct-1087.5670. Found-1087.5725.10484] ?H NMR (400 MHz, Chloroform-d) oe 6.45 (dd, J=14.4, 10.9 Hz, 1H), 6.22 (dd, J=14.5, 10.6 Hz, 1H), 6.13 (dd, J=14.6, 10.5 Hz, 1H), 5.8 (d, J=10.8 Hz, 1H), 515 (dd, i=14.7, 9.8 Hz, 1H), 5.23-5.17 (m, 1H), 5.10 (d, J=9.8 Hz, 1H), 4.67 (m, 2H), 4.47 (d, J=1.8 Hz, 1H), 4.18-4.04 (m, 2H), 4.03-3.91 (m, 1H), 3.72 (d, J=6.5 Hz, 1H), 3.68-3.48 (m, 2H), 3.38 (m, 4H), 3.28 (s, 3H), 3.26-3.12 (m, 2H), .12-2.91 (m, 4H), 2.74 (m, HI), 2.48-2.26 (m, 3F1), 2.26- 2.12 (m, 3H), 2.12-2.04 (m, 2H), 1.87 (s, 3H), 1.85-1.72 (m, 4H), 1.72-1.54 (m, 12H), 1.54-1.43 (m, 6H), 1.43-1.33 (m, 3H), 1.33-1.21 (m, 2H), 1.21-1.09 (m, 2H), 1.03 (m, 7H),1.00-0.78 (m, 9H), 0.72 (q, J=11.9 Hz, 1H).10485] The second eluting peak fractions were pooled and reduced to about volume on the rotary evaporatot The remaining solution was made basic with saturated aqueous NaHCO3. The mixture was extracted several times with ethyl acetate. The organic extracts were combined, dried over Na2504, decanted and concentrated to give Example 15 (0.010 g, 7.51 tmol, 5.02% yield) as a white solid.Example 1510486] ESIMS [M+NH4] 1082.8 [M-H] 1063.8.10487] ?H NMR (400 MHz, Chloroform-d) oe 6.36 (dd,J=19.2, 10.3 Hz, 1H), 6.13 (m, 1H), 6.04-5.84 (m, 1H), 5.65(m, 1H), 5.32 (m, 1FI), 6.21 (m, 1FI), 5.11 (m, 1?H), 4.1 (dd,i=13.7, 7.5 Hz, 1H), 4.21-4.03 (m, IH), 3.83 (dd, J=15.2, 5.1Hz, 2H), 3.74 (d, J?=13.2 Hz, 1H), 3.59 (dq, J=10.9, 6.8, 5.6Hz, 2H), 3.52 (d, J=7.1 Hz, 1H), 3.46-3.33 (m, 7H), 3.30 (m,3H), 3.18 (m, 3H), 3.10-2.82 (m, 3H), 2.39 (t, J=4.1 Hz, 1112.28(m,311),2.14(m,3H), 1.90-1.77(m,4H), 1.74(m,4H
With the rapid development of chemical substances, we look forward to future research findings about 1,1-Dioxo-isothiazolidine
Reference£º
Patent; NOVARTIS AG; BONAZZI, Simone; CONNOLLY, Michael; GLASS, David Jonathan; MIHALIC, Manuel; PATTERSON, Andrew William; ROGGO, Silvio; SHAVLAKADZE, Tea; (68 pag.)US2019/92788; (2019); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com