401564-36-1

Basic information

• Product Name: (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester
• Synonyms: (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester;1-Pyrrolidinecarboxylic acid, 4-oxo-2-(3-thiazolidinylcarbonyl)-, 1,1-diMethylethyl ester, (2S)-;(2S)-4-oxo-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidine-1-carboxylate;(S)-tert-Butyl 4-oxo-2-(thiazolidine-3-carbonyl)pyrrolidine-1-carboxylate;(2S)-tert-butyl 4-hydroxy-2-(thiazolidine-3-carbonyl)pyrrolidine-1-carboxylate;Teneligptin interMediate B;tert-butyl 4-oxo-2-(thiazolidine-3-carbonyl)pyrrolidine-1-carboxylate;(2S)-4-Oxo-2-(thiazolidine-3-carbonyl)-pyrrolidine-1-carboxylic acid t-butyl ester
• CAS NO: 401564-36-1
• Molecular Formula: C₁₃H₂₀N₂O₄S
• Molecular Weight: 302.38978
• EINECS: 1592732-453-0
• Mol File: 401564-36-1.mol
• Article Data: 17

Chemical Properties

• Boiling Point: 492℃
• Flash Point: 251℃
• Appearance: /
• Density: 1.305
• Storage Temp.: 2-8°C
• PKA: -1.22±0.20(Predicted)
• CAS DataBase Reference: (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester(401564-36-1)
• EPA Substance Registry System: (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester(401564-36-1)

Safety Data

• Hazardous Substances Data: 401564-36-1(Hazardous Substances Data)

Usage

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.

Upstream product

• 401564-30-5 3-[(2S,4R)-1-tert-butoxycarbonyl-4-hydroxy-2-pyrrolidinylcarbonyl]-1,3-thiazolidine 
• 13726-69-7 (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid 
• 144-55-8 sodium hydrogencarbonate 
• 504-78-9 1,3-thiazolidine 
• 84348-37-8 N-tert-butoxycarbonyl-4-oxo-L-proline 
• 24424-99-5 di-tert-butyl dicarbonate 
• 51-35-4 4R-4-hydroxyproline 
• 50-00-0 formaldehyd 
• 156-57-0 2-mercaptoethylamine hydrochloride 
• 14446-47-0 thiazolidine hydrochloride 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 
• 102195-80-2 (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 618-27-9 hydroxy L-proline 

Downstream Products

• 401566-08-3 3-[(2S,4S)-4-(4-benzyl-1-piperazinyl)-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl]-1,3-thiazolidine 
• 401566-80-1 tert-butyl (2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]-2-(1,3-thiazolidin-3-ylcarbonyl)pyrrolidine-1-carboxylate 
• 760937-92-6 3-{(2S,4S)-1-(1,1-dimethylethyloxycarbonyl)-4-[4-(3-methyl-1-phenyl-1H-pyrazole-5-yl)piperazin-1-yl]pyrrolidine-2-ylcarbonyl}thiazolidine 
• 401566-91-4 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(4-phenylthiazol-2-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine 
• 503146-73-4 3-((2S,4S)-1-tert-butoxycarbonyl-4-{4-[1-(4-fluorophenyl)-3-methyl-5-pyrazolyl]-1-piperazinyl}-2-pyrrolidinylcarbonyl)-1,3-thiazolidine 
• 503147-82-8 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(3-trifluoromethyl-1-phenyl-5-pyrazolyl)-1-piperazinyl]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine 
• 503146-46-1 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(1-phenyl-5-pyrazolyl)-1-piperazinyl]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine 
• 401566-98-1 C₂₄H₄₀N₈O₃S 
• 401566-86-7 C₂₆H₃₆N₆O₃S 
• 503149-14-2 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(3-trifluoromethyl-1-phenyl-5-pyrazolyl)piperidino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine 
• 503149-26-6 3-{(2S,4S)-1-tert-butoxycarbonyl-4-[4-(1-phenyl-1H-tetrazol-5-yl)piperidino]-2-pyrrolidinylcarbonyl}-1,3-thiazolidine 
• 503147-18-0 3-((2S,4S)-1-tert-butoxycarbonyl-4-{4-[1-(4-cyanophenyl)-3-methyl-5-pyrazolyl]-1-piperazinyl}-2-pyrrolidinylcarbonyl)-1,3-thiazolidine 
• 503147-09-9 3-((2S,4S)-1-tert-butoxycarbonyl-4-{4-[1-(4-chlorophenyl)-3-methyl-5-pyrazolyl]-1-piperazinyl}-2-pyrrolidinylcarbonyl)-1,3-thiazolidine 
• 503146-85-8 3-((2S,4S)-1-tert-butoxycarbonyl-4-{4-[1-(2-fluorophenyl)-3-methyl-5-pyrazolyl]-1-piperazinyl}-2-pyrrolidinylcarbonyl)-1,3-thiazolidine 

Relevant articles and documents

Teneligliptin intermediate crystal form II and preparation method thereof

The invention discloses a teneligliptin intermediate. The chemical name of the teneligliptin intermediate is (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidine carboxylic acid tert-butyl ester, and the structural formula of the teneligliptin intermediate is represented by a formula I. Another purpose of the invention is to provide a crystal form II of the teneligliptin intermediate compound represented by the formula I. The X-ray powder diffraction pattern of the crystal form II has the characteristic peaks at 2[theta] value of 7.00+/-0.2 degrees, 9.20+/-0.2 degrees, 13.98+/-0.2 degrees, 16.24+/-0.2 degrees, 20.16+/-0.2 degrees, 21.02+/-0.2 degrees, 22.42+/-0.2 degrees and 30.22+/-0.2 degrees. The method has the advantages that the intermediate can be highly purified, a sample with the purity of 99.50% or above can be obtained, the method has important significance in improving the quality of the teneligliptin, and the preparation process is simple and suitable for industrial production.

Synthesis method of teneligliptin key intermediate

The invention discloses a synthesis method of a teneligliptin key intermediate, and relates to the technical field of synthesis, in particular to a synthesis method of a teneligliptin key intermediate(2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester. According to the synthesis method, L-hydroxyproline is subjected to an esterification reaction to obtain a compound 1; the compound 1 is protected by t-butyloxycarboryl to obtain a compound 2; the compound 2 is subjected to an oxidation reaction to obtain a compound 3; the compound 3 and thiazolidine are subjected to an ammonia ester exchange reaction to obtain a compound 4. According to the method, a synthesis route suitable for industrial production is designed aiming at the teneligliptin key intermediate,the complexity of the operation is lowered, expensive dehydration reagents are also avoided, the yield is high, the cost is low, and the synthesis method is suitable for industrial application and popularization.

Industrial production method of teneligptin intermediate

The invention relates to the technical field of biochemical engineering, in particular to an industrial production method of a teneligptin intermediate (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester. The method comprises the following steps: oxidizing a raw material N-Boc-hydroxyproline through an oxidizing agent in the presence of a catalyst; performing quenching with water after reaction ends, singly treating water phase in a waste water treatment pipeline, and concentrating organic phase, so as to obtain a product N-Boc-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester crude product, and performing recrystallization on the crude product through a solvent, so as to obtain a finished product. Compared with the prior art,the industrial production method has the advantages that high-quality (2S)-4-oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester can be efficiently and stably produced, the purity is greater than 99 percent, unknown single impurity is smaller than 0.3 percent, and three-waste treatment reach the standards.