(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester Chemical Properties

Boiling point:

492℃

Density 

1.305

Flash point:

251℃

storage temp. 

2-8°C

solubility 

Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

pka

-1.22±0.20(Predicted)

form 

Solid

color 

Pale Yellow to Light Yellow

(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester Usage And Synthesis

Uses

(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic Acid 1,1-Dimethylethyl Ester is an intermediate used to prepare dipeptidyl peptidase IV (DPP-IV) inhibitors.

Synthesis

To (2S)-1-tertbutyloxycarbonyl-4-oxa-tetramethyleneimine-2-carboxylic acid (60.0kg), thiazolidine (30.3kg) and the solution of N-diisopropylethylamine (118kg) in ethyl acetate (595kg), adds the solution of 28w% propyl phosphonous acid anhydride (cyclic trimer) in ethyl acetate (446kg) at 2 ℃-7 ℃, and reaction mixture is stirred 2 hours at 2 ℃-4 ℃.To this reaction mixture, add 15w% aqueous citric acid solution (600kg) for distributing, and ethyl acetate for water layer (271kg) is extracted.
The ethyl acetate layer obtaining is mixed, and use successively 10w% ammonium dibasic phosphate aqueous solution (600kg) and water (300kg) washing. Ethyl acetate layer is concentrated into residual quantity 300L, normal heptane (739kg), 23 ℃ of-25 ℃ of interpolations, and is stirred this mixture 1 hour at 23 ℃-25 ℃, and stir 2 hours at 1 ℃-5 ℃.
The crystal of precipitation is collected by filtration, is used normal heptane (164kg) washing drying under reduced pressure to produce (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester (67.8kg, yield 86%).

(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester(401564-36-1)Related Product Information

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