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

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

Used in Pharmaceutical Industry:
(2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester is used as an intermediate for the preparation of dipeptidyl peptidase IV (DPP-IV) inhibitors. These inhibitors play a crucial role in the treatment of type 2 diabetes by regulating glucose levels in the body. (2S)-4-Oxo-2-(3-thiazolidinylcarbonyl)-1-pyrrolidinecarboxylic acid tert-butyl ester's unique structure allows for the development of potent and selective DPP-IV inhibitors, which can help improve the management of diabetes and its associated complications.

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 
• 52-89-1 l-cysteine hydrochloride 
• 618-27-9 hydroxy L-proline 
• 87691-27-8 N-tert-butoxycarbonyl-L-cis-4-hydroxyproline 
• 50-00-0 formaldehyd 
• 156-57-0 2-mercaptoethylamine hydrochloride 
• 102195-80-2 (S)-1-tert-butyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate 
• 1499-56-5 (R)-4-hydroxy-L-proline ethyl ester 

Downstream Products

• 401565-11-5 3-((2S,4S)-1-tert-butoxycarbonyl-4-(4-chlorophenyl)amino-2-pyrrolidinylcarbonyl)-1,3-thiazolidine 
• 401565-10-4 3-[(2S,4S)-4-(p-anisidino)-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl]-1,3-thiazolidine 
• 401565-09-1 3-((2S,4S)-4-anilino-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl)-1,3-thiazolidine 
• 401565-13-7 3-[(2S,4S)-1-tert-butoxycarbonyl-4-(3-chloro-4-methoxyphenyl)amino-2-pyrrolidinylcarbonyl]-1,3-thiazolidine 
• 401566-06-1 C₂₃H₃₄N₄SO₃ 
• 401566-08-3 3-[(2S,4S)-4-(4-benzyl-1-piperazinyl)-1-tert-butoxycarbonyl-2-pyrrolidinylcarbonyl]-1,3-thiazolidine 
• 401566-09-4 C₃₀H₄₀N₄SO₃ 
• 401566-12-9 C₂₄H₃₆N₄O₄S 
• 401566-16-3 C₂₃H₃₃N₄O₃SF 
• 401566-19-6 C₂₃H₃₃N₄O₃SCl 
• 401566-18-5 C₂₃H₃₃N₄O₃SCl 
• 401566-17-4 C₂₃H₃₃N₄O₃SCl 
• 401566-20-9 C₂₃H₃₃N₄O₃SBr 
• 401566-15-2 C₂₃H₃₃N₅O₅S 

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.

Method for synthesizing tert-2-(3- (2S)-4- butyl)-1- ester of n-oxo-isothiazole alkyloxycarbonylpyrrolidinecarboxylic acid (by machine translation)

The technical scheme of the present (2S) - 4 - invention is that the following) - 1 - technical scheme of the present invention, is that the compound is obtained. by the continuous production of the: compound having L - the following beneficial, effects: the Boc compound is obtained II, from the following technical scheme III, No.No. STR3, No.No. IV; The technical proposal of the present invention is the following technical proposal: II No.No. STR3 III. No., No. The following technical II, proposal III Boc - L - of the present, N - Boc - 4 - IV invention is the following (2S) - 4 -) - 1 - technical proposal: No.No. STR8. No. II No.No. :(1) STR8 III, No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2, No.No.No. STR8No.No.No.No. .(2) STR8No., No.No.No.. STR8No., No.No.No., STR2No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR7No.No.No.No. ST (by machine translation)

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.

MANUFACTURING METHOD OF PROLINE AMIDE COMPOUND

PROBLEM TO BE SOLVED: To provide an industrially advantageous manufacturing method of teneligliptin useful as an antidiabetic drug or the like and a synthesis intermediate. SOLUTION: There is provided a manufacturing method of a thiazolidine derivative represented by the formula (2a) using a following condensation reaction. The compound represented by the formula (2a) is useful as a manufacturing intermediate of teneligliptin. DIPEA represents N,N-diisopropylethylamine. SELECTED DRAWING: None COPYRIGHT: (C)2019,JPOandINPIT

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.

A (S)- 4 - oxo - 2 - (thiazolidine - 3 - carbonyl) pyrrolidine - 1 - carboxylic acid tert-butyl preparation method

The invention relates to the technical field of synthesis of drug intermediates, in particular relates to the technical field of preparation of a heterocyclic compound, and specifically discloses a preparation method of (S)-4-oxo-2-(thiazolidine-3-carbonyl) pyrrolidone-1-carboxylic acid tert-butyl ester. The preparation method comprises the following steps: reacting N-Boc-4-oxo-L-proline and cysteamine hydrochloride as raw materials with formaldehyde aqueous solution under the action of a coupling agent and an acid-binding agent, and performing nucleophilic substitution to obtain (S)-4-oxo-2-(thiazolidine-3-carbonyl) pyrrolidone-1-carboxylic acid tert-butyl ester. By adopting the preparation method, the operation condition is easy to control, the raw materials are easy to obtain, the reaction step is short, and the product can be obtained by a one-pot method by virtue of one-step reaction, and the method is high in yield, short in cycle, low in cost, less in pollution and suitable for industrial production.

Method for preparing hydrobromic acid teneligliptin

The invention provides a method for preparing hydrobromic acid teneligliptin. The method includes steps of preparing L-hydroxyproline; mixing the L-hydroxyproline and sodium bicarbonate with each other to obtain mixtures, dissolving the mixtures in water, adding acetone into the water, dropping di-tert-butyl dicarbonate into the water, carrying out room-temperature reaction overnight and then treating reaction products to obtain t-butyloxycarboryl-N-hydroxyproline; preparing t-butyloxycarboryl-N-4-oxo-proline from the t-butyloxycarboryl-N-hydroxyproline; preparing (2S)-4-oxo-2-(3-thiazolidine carbonyl)-1-pyrrolidine carboxylic acid tert-butyl ester from the t-butyloxycarboryl-N-4-oxo-proline; preparing compounds III from compounds IV; preparing compounds II from the compounds III; preparing compounds 1-(3-methyl-1-phenyl-1H-pyrazole-5-base) piperazine from the compounds II; preparing intermediates I; preparing the hydrobromic acid teneligliptin from the intermediates I. The method has the advantages that the method is low in cost, and the cost of the method is only two-thirds of the cost of an existing method in the prior art; the yield of the hydrobromic acid teneligliptin is higher than 95%, and the purity of the hydrobromic acid teneligliptin is higher than 98%.

PROCESS FOR THE PREPARATION OF (4R)-1-(TERT-BUTOXYCARBONYL)-4-HYDROXY-L-PROLINE

The present invention provides a process for the preparation of (4R)-1-(tert- butoxycarbonyl)-4-hydroxy-L-proline of Formula IV. The present invention also provides a process for the preparation of {(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl) piperazin-1-yl] pyrrolidin-2-yl}(1,3-thiazolidin-3-yl) methanone of Formula II, or salts thereof, using (4R)-1-(tert-butoxycarbonyl)-4-hydroxy-L-proline of Formula IV.

For the preparation of pyrazole derivatives

The present invention provides a prolinamide compound useful as a drug or the like and an industrially advantageous method for producing a piperazinyl pyrazole compound that is a production intermediate of the prolinamide compound. Specifically, the invention is a method for producing a compound represented by general formula (1) as represented by the following formula (where the symbols in the formula are the same as defined in the specification) or a salt thereof, wherein a compound represented by general formula (2) is produced, a pyrazole ring being formed via a reaction between a compound represented by general formula (3) and phosphorus pentasulfide; and, once the compound represented by general formula (2) is deprotected, a carboxylate of a compound represented by general formula (6) is produced, the compound obtained by forming a carboxylic acid and a salt.

PROCESS FOR THE PREPARATION OF N-PROTECTED (5S)-5-(1,3-THIAZOLIDIN-3-YLCARBONYL)PYRROLIDIN-3-ONE

The present invention provides a process for the preparation of an N-protected (55)-5-(l,3-thiazolidin-3-ylcarbonyl)pyrrolidin-3-one of Formula III. The invention also provides a process for the preparation of {(25',45)-4-[4-(3-methyl-l-phenyl-lH-pyrazol-5- yl)piperazin-l-yl]pyrrolidin-2-yl}(l,3-thiazolidin-3-yl)methanone, or salts thereof, using the N-protected (55)-5-(l,3-thiazolidin-3-ylcarbonyl)pyrrolidin-3-one of Formula III. (III)