38074-72-5

Usage

Uses

Used in Pharmaceutical Industry:
1-(CHLOROACETYL)-L-PROLINE METHYL ESTER is used as an impurity in the production of Vildagliptin, an oral anti-hyperglycemic agent. It is utilized for its role in the synthesis of Vildagliptin, which inhibits dipeptidyl peptidase 4 (DPP-4), a serine exopeptidase enzyme. This inhibition helps in managing blood glucose levels in type 2 diabetes patients.
Additionally, Vildagliptin and other gliptins have been found to possess positive cardiovascular and anti-inflammatory effects, making them valuable in the treatment and management of type 2 diabetes and its associated complications.

Upstream product

• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 
• 79-04-9 chloroacetyl chloride 
• 543-27-1 isobutyl chloroformate 
• 67-56-1 methanol 
• 147-85-3 L-proline 
• 2133-40-6 L-proline methyl ester monohydrochloride 
• 79-11-8 chloroacetic acid 

Downstream Products

• 197453-30-8 (S)-2-((S)-1,4-Dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-methyl-pentanoic acid benzyl ester 
• 225645-11-4 1-(N-benzyl-N-methylglycyl)-(S)-proline methyl ester 
• 565453-39-6 (S)-1-[2-(3-hydroxyadamantan-1-ylamino)acetyl]pyrrolidine-2-carboxylic acid amide 
• 274901-16-5 vildagliptin 
• 93643-24-4 (S)-octahydropyrrolo[1,2-a]pyrazine 
• 1549877-31-7 dimethyl 6-benzyl-5,9-dioxo-2,3,5,6-tetrahydro-1H-6,8a-(epiminomethano)indolizine-7,8-dicarboxylate 
• 1549877-25-9 dimethyl 2-benzyl-5-(3-isocyanatopropyl)-6-methoxypyridine-3,4-dicarboxylate 
• 1549877-20-4 C₁₅H₁₆N₂O₂ 

Relevant academic research and scientific papers

Carbostyril carboxylic compounds and intermediates, preparation method and application thereof

The invention discloses carbostyril carboxylic compounds and hydrochlorides thereof and also discloses a preparation method of the compounds and the hydrochlorides thereof as well as an application of the compounds and the hydrochlorides thereof in preparing gram-positive bacterium-preventing or gram-negative bacterium-preventing drugs. Moreover, the invention discloses intermediates for preparing the compounds and a preparation method of the intermediates.

A preparation method of the peculiar smell impurity

A disclosed preparation method for a vildagliptin impurity comprises the following steps: (1) reacting methyl L-prolinate with chloroacetyl chloride under an alkali condition to generate a compound I; (2) performing condensation reaction on the compound 1 and 3-amino-1-hydroxyadamantane to generate a compound 2; and (3) performing a self condensation reaction on the compound 2 under an alkali condition to obtain vildagliptin related compound 2. According to the vildagliptin related compound 2 synthetic method, methyl L-prolinate is taken as the raw material and is reacted with chloroacetyl chloride under the alkali condition for preparing the compound 1, the compound 1 is condensed with 3-amino-1-hydroxyadamantane for generating the compound 2, and the compound 2 is subjected to the self condensation reaction under the alkali condition for obtaining the vildagliptin related compound 2. The synthetic method is simple, reaction conditions are mild, operationality is high, a product according with quality standard is obtained through simple purification, and research and development cost is effectively reduced.

NOVEL ECONOMIC PROCESS FOR VILDAGLIPTIN

The present invention relates to a commercially viable novel process for manufacturing Vildagliptin in high yield with high chemical and chiral purity.

Synthesis of 2-pyridones by cycloreversion of [2.2.2]- bicycloalkene diketopiperazines

A general strategy for the conversion of [2.2.2]-diazabicyclic alkene structures to 2-pyridone aromatic heterocyclic products is reported. The reaction sequence starts from 2,5-diketopiperazine (DKP) derivatives, is compatible with both aromatic and aliphatic aldehyde components, and can intercept either intra- or intermolecular cycloaddition manifolds. Priming of one aza-bridging function in the intermediate [2.2.2]-DKP scaffold permits cycloreversion (microwave heating) and selective extrusion of cyanate derivatives leading to the formation of 2-pyridone structures. Progress toward the synthesis of louisianin A and B, antiproliferative 2-pyridone natural products, is also disclosed.

Enantioselective synthesis of (+)-malbrancheamide B

The asymmetric total synthesis of the chlorinated [2.2.2]-diazabicyclic indole alkaloid (+)-malbrancheamide B is reported. Key to the synthesis is a domino reaction sequence that employs an aldol condensation, alkene isomerization, and intramolecular Diels-Alder cycloaddition. Diastereofacial selection between the azadiene stereofaces is enforced with a chiral aminal auxiliary. A formal 7-step (longest linear route) synthesis of (±)-malbrancheamide B is also reported.

SYNTHESIS OF [2.2.2]-DIAZABICYCLIC RING SYSTEMS

Herein we describe compositions and methods for the synthesis of [2.2.2]-diazabicyclic structures comprising a domino reaction sequence involving aldol condensation, alkene isomerization, and intramolecular hetero-Diels-Alder cycloaddition. Excellent diastereofacial control during the cycloaddition is enforced with a removable chiral phenyl aminal diketopiperazine substituent. The reaction sequence rapidly generates molecular complexity and is competent with both enolizable and non-enolizable aldehyde substrates. This method provides an efficient route to [2.2.2]-diazabicyclic structures, common to bioactive prenylated indole alkaloids such as the brevianamides and stephacidins.

Chemoselective formation of successive triazole linkages in one pot: "Click-click" chemistry

A methodology for the successive regiospecific "clicking" together of three components in one pot via two triazole linkages is reported. The protocol utilizes copper(I)-mediated alkyne-azide cycloaddition reactions combined with a silver(I)-catalyzed TMS-

Pharmaceutical compositions comprising metal complexes

A compound of the formula [Ma(XbL)cYdZe]nt±Formula I wherein: M is a metal ion or a mixture of metal ions; X is a cation or a mixture of cations; L is a ligand, or mixture of ligands each containing at least two different donor atoms selected from the elements of Group IV, Group V or Group VI of the Periodic Table; Y is a ligand or a mixture of the same or different ligands each containing at least one donor atom or more than one donor atom selected from the elements of Group IV, Group V or Group VI of the Periodic Table; and Z is a halide or pseudohalide ion or a mixture of halide ions and pseudohalide ions; and wherein: a=1-3; b=0-12; c=0-18; d=0-18; e=0-18; and n=0-10; provided that at least one of c, d and e is 1 or more; wherein c is 0: b is also 0; wherein a is 1: c, d and e are not greater than 9; and wherein a is 2: c, d and e are not greater than 12.

Photoinduced electron transfer (PET) promoted oxidative activation of 1- (N-benzyl-N-methylglycyl)-(S)-prolinol: Development of novel strategies towards enantioselective syntheses of α-amino acids, their N-methyl derivatives and α-hydroxy acids employing

PET activation of 1-(N-benzyl-N-methylglycyl)-(S)-prolinol (1) in dry acetonitrile, utilizing 1,4-dicyanonaphthalene (DCN) as a light-harvesting electron-acceptor and methyl viologen (MV++) as an electron-transfer mediator, leads to the formati

Synthesis and Utilisation of Chiral 3-N- Benzyl-N-methylaminoperhydropyrrolo-[2,1-c][1,4]oxazin-4-one as a Novel Precursor for the Enantioselective Synthesis of α-Amino Acids and Their N-Methyl Derivatives

α-Amino acids and their N-methyl derivatives are synthesised in good optical purity by the nucleophilic alkylation of chiral 3-N-benzyl-N-methylaminoperhydropyrrolo[2,1-c][1,4]oxazin-4-one (1). The chiral auxiliary, L-prolinol, is isolated in recyclable f