Process for synthesizing chiral thiazolidine-2-thioketone

A synthesis method and compound technology, which is applied in the field of synthesis of chiral thiazolidine-2-thione compounds, can solve the problems of long reaction time, expensive raw materials, difficult to avoid by-product oxazolidine-2-thione, etc. , to achieve the effect of simple operation and low cost

Inactive Publication Date: 2007-04-25
DONGHUA UNIV +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] The former method is divided into two steps, and the raw materials used in the first step are relatively expensive
The latter method, the reaction time is longer, because the flash point and the boiling point of carbon disulfide are a

Method used

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  • Process for synthesizing chiral thiazolidine-2-thioketone
  • Process for synthesizing chiral thiazolidine-2-thioketone
  • Process for synthesizing chiral thiazolidine-2-thioketone

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Experimental program
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Effect test

Embodiment 1

[0023]

[0024] Add toluene (20mL) to the chiral oxazolidinone 1 (1.63g, 10mmol) under stirring at room temperature, after complete dissolution, add phosphorus pentasulfide (5.55g, 25mmol), heat and reflux for 3 hours, T.L.C shows that the reaction is complete, stop stirring, Let it stand for 10 minutes, and decant the supernatant liquid while it is hot. The remaining solid was cooled to room temperature, placed in an ice bath, and saturated NaHCO was slowly added under rapid stirring. 3 solution, the solid was completely dissolved, the solution was neutral, and then, ethyl acetate was added for extraction (20mL×3). The extracted organic phase was combined with the decanted clear liquid, and successively washed with saturated NaHCO 3 solution (40mL), water (40mL), washed with saturated brine (40mL), anhydrous Na 2 SO 4 After drying, the solvent was evaporated under reduced pressure at room temperature to obtain (R)-4-phenyl-thiazolidine-2-thione 2 (white solid, 1.72 g, y...

Embodiment 2

[0026]

[0027] Toluene (20mL) was added to the chiral oxazolidinone 3 (1.77g, 10mmol) under stirring at room temperature. After complete dissolution, phosphorus pentasulfide (5.55g, 25mmol) was added, and heated to reflux for 3 hours. T.L.C showed that the reaction was complete, and the stirring was stopped. Let it stand for 10 minutes, and decant the supernatant liquid while it is hot. The remaining solid was cooled to room temperature, placed in an ice bath, and saturated NaHCO was slowly added under rapid stirring. 3 solution, the solid was completely dissolved, the solution was neutral, and then, ethyl acetate was added for extraction (20mL×3). The extracted organic phase was combined with the decanted clear liquid, and successively washed with saturated NaHCO 3 solution (40mL), water (40mL), washed with saturated brine (40mL), anhydrous Na 2 SO 4 Drying and concentration to remove the solvent gave (S)-4-benzyl-thiazolidine-2-thione 4 (light yellow solid, 1.80 g, yi...

Embodiment 3

[0029]

[0030] Add toluene (20mL) to the chiral oxazolidinone 5 (1.29g, 10mmol) under stirring at room temperature. After complete dissolution, add phosphorus pentasulfide (5.55g, 25mmol), heat and reflux for 3 hours, T.L.C shows that the reaction is complete, stop stirring, Let stand for 10 minutes, and decant the supernatant liquid while hot. The remaining solid was cooled to room temperature, placed in an ice bath, and saturated NaHCO was slowly added under rapid stirring. 3 solution, the solid was completely dissolved, the solution was neutral, and then, ethyl acetate was added for extraction (20mL×3). The extracted organic phase was combined with the decanted clear liquid, and successively washed with saturated NaHCO 3 solution (40mL), water (40mL), washed with saturated brine (40mL), anhydrous Na 2 SO 4 After drying and concentration to remove the solvent, (S)-4-isopropyl-thiazolidine-2-thione 6 was obtained (yellow oil, 1.30 g, yield 81%). [α] D 19 -35.72° (c0...

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Abstract

The invention discloses a synthesizing method of chiral thiazolidine-2-thionone compound with structure formula 1, which is characterized by the following: refluxing chiral thiazolidine ketone and phosphorus pentasulfide in the organic solvent; simplifying the synthesizing method; controlling reacting condition easily; fitting for industrial manufacturing.

Description

technical field [0001] The invention relates to the field of medicine synthesis, in particular to a synthesis method of chiral thiazolidine-2-thione compounds. Background technique [0002] Chiral thiazolidine-2-thione compounds are used as chiral prosthetic groups for the synthesis of chiral compounds in the 1980s and 1990s (see (a) Nagao, Y.; Hagiwara, Y.; Kumagai, T.; et al.J.Org.Chem., 1986, 51(12):2391-2393. (b) Nagao, Y.; Dai, W.M.; Ochiai, M.; Shiro, M.J.Org.Chem., 1989, 54(22):5211-5217.(c) Nagao, Y.; Dai, W.M.; Ochiai, M.; et al.J.Org.Chem., 1990, 55(4):1148-1156.(d) Nam, K.S.; Nagao, Y.; B. Kor. Chem. Soc. 1997, 18(11):1208-1210.). Among them, 4-monosubstituted thiazolidine-2-thione prosthetic groups have attracted more attention in recent years due to their excellent performance in asymmetric aldol reactions. In asymmetric reactions, compared with the traditional Evans prosthetic group (oxazolidin-2-one prosthetic group), the 4-monosubstituted thiazolidine-2-th...

Claims

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Application Information

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IPC IPC(8): C07D277/36
Inventor 陈志龙余秀峰田娟李焰朱泉
Owner DONGHUA UNIV
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