84793-24-8

Usage

Uses

Used in Pharmaceutical Industry:
Ethyl (S)-2-[(S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutyrate is used as an impurity in the production of Enalapril, an antihypertensive medication and an angiotensin-converting enzyme (ACE) inhibitor. It helps in the development and manufacturing process of the drug, ensuring its efficacy and safety for patients.

InChI:InChI=1/C16H19NO5/c1-3-21-15(19)13(10-9-12-7-5-4-6-8-12)17-11(2)14(18)22-16(17)20/h4-8,11,13H,3,9-10H2,1-2H3/t11-,13-/m0/s1

Upstream product

• 75-44-5 phosgene 
• 82717-96-2 [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine 
• 530-62-1 1,1'-carbonyldiimidazole 
• 32315-10-9 bis(trichloromethyl) carbonate 

Downstream Products

• 83435-61-4 N-(2,3-dihydro-1H-inden-2-yl)-N--L-alanyl>-glycine t-butyl ester 
• 87679-46-7 C₃₀H₃₈N₂O₅ 
• 82717-96-2 [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine 
• 76420-72-9 enalaprilate 
• 75847-73-3 enalapril 
• 115729-52-7 (S)-2-((3S,8aS)-3-Methyl-1,4-dioxo-hexahydro-pyrrolo[1,2-a]pyrazin-2-yl)-4-phenyl-butyric acid ethyl ester 
• 82586-56-9 tert-butyl (S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 852921-57-4 N-[1-(S)-carbethoxy-3-phenylpropyl]-(S)-alanyl-2R,3aS,7aR-octahydroindole-2-carboxylic acid 
• 87679-37-6 trandolapril 
• 129939-63-5 ramipril 
• 87333-19-5 Ramipril 
• 847202-70-4 ethyl (2S)-2-(((1S)-2-((2S)-2-(((1S,2S,5S,6R)-6-(nitrooxy)-4,8-dioxabicyclo(3.3.0)oct-2-yl)oxycarbonyl)pyrrolidinyl)-1-methyl-2-oxoethyl)amino)-4-phenylbutanoate 
• 928142-34-1 t-butyl-(4S)-3-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1-methyl-2-oxo-4-imidazolidinecarboxylate hydrochloride 
• 87269-88-3 2--L-alanyl>-(1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid benzylester 

Relevant academic research and scientific papers

PROCESS FOR PRODUCING ORGANIC COMPOUND

A process for producing an organic compound using a flow reactor for a first reaction in which a raw material liquid A and a raw material liquid B are mixed, and reacted in a reactor unit, and a flow reactor for a second reaction in which a first reaction

Continuous Flow Synthesis of ACE Inhibitors From N-Substituted l-Alanine Derivatives

A strategy for the continuous flow synthesis of angiotensin converting enzyme (ACE) inhibitors is described. An optimization effort guided by in situ IR analysis resulted in a general amide coupling approach facilitated by N-carboxyanhydride (NCA) activation that was further characterized by reaction kinetics analysis in batch. The three-step continuous process was demonstrated by synthesizing 8 different ACE inhibitors in up to 88 % yield with throughputs in the range of ≈0.5 g h?1, all while avoiding both isolation of reactive intermediates and process intensive reaction conditions. The process was further developed by preparing enalapril, a World Health Organization (WHO) essential medicine, in an industrially relevant flow platform that scaled throughput to ≈1 g h?1.

PROCESS FOR PRODUCING ORGANIC COMPOUND

The present disclosure provides a reaction of a chlorine-containing compound using a flow reactor which is less restricted by a solvent to be used. In the present disclosure, an organic compound is produced by supplying a reaction substrate having at least one functional group which can react with chlorine and is selected from the group consisting of hydroxy group, a thiol group, an amino group, a carboxyl group, a thiocarboxyl group, and an acid amide group, and a chlorine-containing compound to a flow reactor together with a trialkyl amine having 9 to 40 carbon atoms and an organic solvent, and allowing the reaction substrate and the chlorine-containing compound to react with each other.

Safe and Efficient Phosgenation Reactions in a Continuous Flow Reactor

Phosgene is widely used in organic synthesis owing to its high reactivity, utility, and cost efficiency. However, the use of phosgene in batch processes on the industrial scale is challenging owing to its toxicity. An effective method to minimize reaction volumes and mitigate the safety risks associated with hazardous chemicals is the use of flow reactors. Consequently, we have established a flow reaction system using triphosgene and tributylamine, which affords a homogeneous reaction that avoids clogging issues. In addition, we have demonstrated that this methodology can be applied to a wide variety of phosgene reactions, including the preparation of pharmaceutical intermediates, in good to excellent yields.

PROCESS FOR THE SYNTHESIS OF AN ACE INHIBITOR

A process for the synthesis of trandolapril which comprises condensing N-[I-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride with trans octahydro-1H- indole-2-carboxylic acid in a first organic solvent comprising a water immiscible inert organic solvent and in the presence of a base, and isolating trandolapril from a second organic solvent. N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride may also be condensed with (2S,3aR,7aS) octahydro-1H-indole-2-carboxyIic acid in a first organic solvent and in the presence of a base, and trandolapril isolated. There is also provided a process for the resolution of racemic trans octahydro-1H-indole-2-carboxylc acid.

Process for the preparation of intermediates of trandolapril and use thereof for the preparation of trandolapril

A process for the preparation of an intermediate of trandolapril, (2S,3aR,7aS)-perhydroindole-2-carboxylic acid of Formula II is provided. Also provided are processes for preparing trandolapril.

METHOD FOR PRODUCING {N-[1-(S)-CARBALKOXY-3-PHENYLPROPYL]-S-ALANYL-2S, 3AR, 7AS-OCTAHYDROINDOL-2-CARBOXYLIC ACID} COMPOUNDS

The invention relates to a method for producing optionally substituted {N-[1-(S)-carbalkoxy-3-phenylpropyl]-S-alanyl-2S, 3aR, 7aS-octahydroindol-2-carboxylic acid} and the pharmaceutically acceptable salts thereof. To this end, a racemic mixture of optionally substituted trans-octahydroindol-2-carboxylic acid is reacted with the N-carboxyanhydride of {N-[1-(S)-alkoxycarbonyl-3-phenylpropyl]-L-alanine}, which is optionally substituted on the phenyl ring, in an appropriate inert solvent, and the obtained optionally substituted {N-[1-(S)-carbalkoxy-3-phenylpropyl]-S-alanyl-2S, 3aR, 7aS-octahydroindol-2-carboxylic acid}, preferably trandolapril, is subsequently isolated, as well as polymorphous forms A and B of trandolapril.

Process for preparing N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride

A process for preparing N-[1- (S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride of the following formula (I), is to react N-[1-(S)-ethyoxy carbonyl-3-phenylpropyl]-L-alanine with XCOOR, wherein X is halogen atom, R is C1-C6/

Process for preparing N-[1-(S)-ethyoxycarbonyl-3-phenylpropyl]-L-ananine N-carboxyanhydride

A process for preparing N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride of the following formula (I), is to react N-[1 -(S)-ethyoxy carbonyl-3-phenylpropyl]-L-alanine with XCOOR, wherein X is halogen atom, R is C1-C6alkyl, to obtain a N-alkoxycarbonyl compound, then reacting with an acyl group activation reagent, finally contact with water. The compound of formula (I) is a key intermediate of ACE inhibitors.

Angiotensin-converting enzyme inhibitors: N-substituted glycine derivatives

We report a series of novel dipeptides, which exhibit potent in vitro angiotensin-converting enzyme (ACE) inhibition. These dipeptides embody N-substituted glycine as the COOH terminus amino acid. The dipeptide L-lysyl-N-(2,3-dihydro-1Hinden-5-yl)glycine,