(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester
- CAS NO.：401564-36-1
- Empirical Formula: C13H20N2O4S
- Molecular Weight: 300.37
- MDL number: MFCD22665915
- EINECS: 813-401-8
- SAFETY DATA SHEET (SDS)
- Update Date: 2025-07-24 18:12:00
What is (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester?
The Uses of (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester
(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%).
Appearence
White to yellow powder
Properties of (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester
| Boiling point: | 492℃ |
| Density | 1.305 |
| Flash point: | 251℃ |
| storage temp. | 2-8°C |
| solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) |
| form | Solid |
| pka | -1.22±0.20(Predicted) |
| color | Pale Yellow to Light Yellow |
Safety information for (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester
| Signal word | Warning |
| Pictogram(s) |
 Exclamation Mark Irritant GHS07 |
| GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
| Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester
(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester manufacturer
SRINI PHARMACEUTICALS PVT LTD
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