5908-62-3, 1,1-Dioxo-isothiazolidine is a thiazolidine compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated
To a stirring solution of Intermediate 1 (2.0 g,2.222 mmol) and isothiazolidine 1,1-dioxide (4.04 g, 33.3 mmol, 15 equivalents) in anhydrous dichloromethane (5.6 mE) was added p-toluenesulphonic acid*H20 (0.042 g, 0.222 mmol, 0.1 equivalent) in one portion. The reaction was stirred at ambient temperature under a nitrogen atmosphere for 34 minutes. The entire reaction mixture was directly chromatographed by over silica (gradient elution from 100% heptane to 40% acetone-heptane) to give a product mixture of both diastereomers in a ratio of about 3:1 by UV absorbance at 279 nm on EC/MS analysis.10415] The diastereomeric mixture was separated by normal phase chromatography on silica (gradient elution from 100% dichloromethane to 40% acetonitrile-dichloromethane).10416] The first eluting diastereomer (Rf 0.23 on silica TEC developed in 30% acetonitrile-dichloromethane) affords Example 1 (5)-diastereomer as a white solid.Example 110417] ESIMS [M+NH4] 1006.7, ESIMS [M-H] 987.8.10418] ?H NMR (600 MHz, Chloroform-d) oe 6.43 (dd,J=14.9, 10.4 Hz, 1H), 6.35 (dd, J=14.9, 10.7 Hz, 1H), 6.16(dd, J=15.1, 10.2 Hz, 1H), 6.06-6.01 (m, 1H), 5.67 (dd,J=15.2, 8.6 Hz, 1H), 5.35 (dd, J=6.4, 1.8 Hz, 1H), 5.26 (d,J=9.6 Hz, 1H), 4.83 (td, J=6.6, 4.7 Hz, 1H), 4.12 (d, J=7.4Hz, 1H), 3.88 (dd, J=11.1, 5.1 Hz, 1H), 3.84-3.77 (m, 1H),3.63-3.60 (m, 2H), 3.51 (d, J=7.5 Hz, 1H), 3.46 (s, 3H),3.45-3.42 (m, 3H), 3.35 (s, 3H), 3.29-3.14 (m, 3H), 3.06-2.96 (m, 2H), 2.93 (ddd, J=10.4, 6.4, 1.5 Hz, 1H), 2.44 (U,J=8.6, 6.2 Hz, 1H), 2.37-2.23 (m, 4H), 2.22-2.14 (m, 2H),2.03 (dt, J12.3, 3.8 Hz, 1H), 1.96 (pd, J6.4, 5.7, 3.5 Hz,2H), 1.92-1.82 (m, 3H), 1.80-1.76 (m, 2H), 1.75 (d, J=1.2Hz, 4H), 1.72 (d, J=3.1 Hz, 1H), 1.68 (d, J=1.3 Hz, 3H),1.65-1.53 (m, 4H), 1.48-1.17 (m, 9H), 1.07 (d, J=6.5 Hz,1H), 1.06 (s, 3H), 1.04 (d, J=7.3 Hz, 3H), 1.01 (d, J=6.6 Hz,3H), 0.99 (dd, J=6.7, 2.3 Hz, 3H), 0.95 (d, J=6.8 Hz, 3H),0.74 (q, J=11.9 Hz, 1H).10419] The second eluting diastereomer (Rf 0. 16 onsilica TEC developed in 30% acetonitrile-dichloromethane)affords Example 2 (R)-diastereomer as a white solidExample 210420] ESIMS [M+NH4] 1006.9, ESIMS [M-H] 988.1.10421] ?H NMR (Chloroform-d) oe 6.48 (dd, J14.7, 10.9Hz, 1H), 6.24 (dd, J=14.6, 10.6 Hz, 1H), 6.16 (dd, J14.9,10.6 Hz, 1H), 6.01 (d, J=11.0 Hz, 1H), 5.38 (dd, J=14.9, 9.8Hz, 1H), 5.23 (dd, J=6.2, 2.0 Hz, 1H), 5.12 (d, J9.9 Hz,1H), 4.73 (dd, J=12.1, 2.9 Hz, 1H), 4.65 (dt, J8.3, 3.9 Hz,1H), 4.14 (d, J=6.7 Hz, 1H), 3.97 (m, 1H), 3.74 (d, J=6.7 Hz,1H), 3.62 (qd, J=13.9, 12.7, 5.5 Hz, 2H), 3.42 (s, 3H), 3.39(m, 1H), 3.31 (s, 3H), 3.24 (ddd, J=12.2, 7.5, 4.6 Hz, 1H),3.10 (td, J=8.2, 3.8 Hz, 1H), 3.08 (s, 1H), 3.02-2.97 (m, 1H),2.97-2.92 (m, 1H), 2.83-2.71 (m, 1H), 2.42 (ddt, J=13.1, 9.5,6.4 Hz, 1H), 2.34 (d, J=4.3 Hz, 1H), 2.31 (s, 1H), 2.28-2.23(m, 1H), 2.22-2.19 (m, 1H), 2.19 (s, 2H), 2.12-2.08 (m, 2H),2.03-1.99 (m, 1H), 1.90 (s, 3H), 1.88 (s, 1H), 1.79 (s, 1H),1.77 (s, 1H), 1.76 (s, 1H), 1.72-1.68 (m, 1H), 1.48 (s, 1H),1.46 (s, 1H), 1.40 (d, J=3.0 Hz, 1H), 1.38 (s, 1H), 1.66 (d, J=3.0 Hz, 2H), 1.64 (d, J=2.9 Hz, 1H), 1.62 (s, 2H), 1.62 (s, 2H), 1.58-1.53 (m, 1H), 1.37 (s, 1H), 1.36 (d, J=2.3 Hz, 1H),1.33 (d, J=2.9 Hz, 1H), 1.30 (dd, J=6.7, 1.8 Hz, 1H), 1.28 (s, 2H), 1.28 (s, 2H), 1.24 (s, 1H), 1.09 (s, 1H), 1.07 (d, J=6.6 Hz, 3H), 1.05 (d, J=6.6 Hz, 3H), 1.01 (d, J=3.2 Hz, 1H), 0.95 (d, J=6.8 Hz, 3H), 0.92 (s, 1H), 0.92-0.90 (m, 3H), 0.88 (d, J=6.8 Hz, 2H), 0.66 (q, J=12.0 Hz, 1H)
5908-62-3 1,1-Dioxo-isothiazolidine 642157, athiazolidine compound, is more and more widely used in various.
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