The thiazolidine compound, cas is 171877-39-7 name is (S)-4-Benzylthiazolidine-2-thione, mainly used in chemical industry, its synthesis route is as follows.
To an ice-bath cold solution of 35 (S)-4-benzylthiazolidine-2-thione13 (18.37g, 87.87mmol) and 36 Et3N (26.66mL, 175.74mmol) in 37 CH2Cl2 (266mL) was added 38 4-phenylbutanoyl chloride (freshly prepared from 39 4-phenylbutyric acid (17.31g, 105.44mmol)). The resulting mixture was stirred at room temperature for 24h. Then brine was added and extracted with CH2Cl2 (3¡Á40mL), the organic layers were washed (brine), dried (Na2SO4) and concentrated. The yellow crude oil was purified through chromatography (silica-gel, hexanes/40 EtOAc (98:2) and (95:5)) to afford 24.76mg (77%); [alphaD25]=+157.80 (c=2.3, CHCl3). IR (NaCl) nu 3025, 2935, 2849, 1603, 1695, 1496, 1454, 1342, 1394, 1359, 1342, 1293, 1264, 1192, 1157, 1135, 1040, 893, 746, 701cm-1. 1H NMR (500MHz, CDCl3) delta 7.16-7.34 (10H, m), 5.33 (1H, ddd, J=4.0, 7.5 and 11.5Hz), 3.38 (1H, ddd, J=6.0, 9.0 and 17.0Hz), 3.33 (1H, dd, J=7.5 and 11.5Hz), 3.13-3.20 (2H, m), 3.01 (1H, dd, J=10.5 and 13.0Hz), 2.84 (1H, d, J=11.5Hz), 2.68 (2H, t, J=7.0Hz). 13C NMR (125MHz, CDCl3) delta 201.06, 173.73, 141.53, 136.56, 129.44, 128.88, 128.53, 128.36, 127.19, 125.96, 68.53, 37.93, 36.79, 35.11, 31.90, 26.43ppm.. HRMS m/z calcd. for C20H21ONS2Na [M+Na+]: 378.0962, found: 378.0970; m/z calcd. for C20H21ONS2K [M+K+]: 394.0702, found: 394.0724.
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Reference£º
Article; Royo, Santiago; Schirmeister, Tanja; Kaiser, Marcel; Jung, Sascha; Rodriguez, Santiago; Bautista, Jose Manuel; Gonzalez, Florenci V.; Bioorganic and Medicinal Chemistry; vol. 26; 16; (2018); p. 4624 – 4634;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com