84793-24-8

Basic information

• Product Name: Ethyl (S)-2-[(S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutyrate
• Synonyms: ECPP-ACA;ETHYL (S)-2-[(S)-4-METHYL-2,5-DIOXO-1,3-OXAZOLIDIN-3-YL]-4-PHENYLBUTYRATE;N-[1-(S)-ETHOXYCARBONYL-3-PHENYLPROPYL]-N-CARBOXY-L-ALANINE ANHYDRIDE (NEPA-NCA);ECPPA-NCA;N-(1-(S)-(+)-ETHOXYCARBONYL-3-PHENYLPRO&;N-[1-(S)-ETHOXYCARBONYL-3-PHENYLPROPYL]-L-ALANINE -N-CARBOXYANHYDRIDE(INTERMEDIATE OF ENALAPRIL);n-[1-(s)-(ethoxycarbonyl)-3-phenylpropyl]-1-alanylcarboxy anhydride;N-(1-(S)-Ethoxy Carbonyl-3-Phenylpropyl)-L-Alanine-N-carboxyanhydried
• CAS NO: 84793-24-8
• Molecular Formula: C₁₆H₁₉NO₅
• Molecular Weight: 305.33
• EINECS: 212-344-0
• Product Categories: (intermediates of enalapril);Alanine Derivatives;Peptide Synthesis;Unnatural Amino Acid Derivatives
• Mol File: 84793-24-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: 69-73 °C(lit.)
• Boiling Point: 414.788 °C at 760 mmHg
• Flash Point: 204.657 °C
• Appearance: /
• Density: 1.223 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.537
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C
• PKA: -2.40±0.40(Predicted)
• BRN: 5608080
• CAS DataBase Reference: Ethyl (S)-2-[(S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutyrate(CAS DataBase Reference)
• NIST Chemistry Reference: Ethyl (S)-2-[(S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutyrate(84793-24-8)
• EPA Substance Registry System: Ethyl (S)-2-[(S)-4-methyl-2,5-dioxo-1,3-oxazolidin-3-yl]-4-phenylbutyrate(84793-24-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-43-41
• Safety Statements: 22-24/25-36-26-37/39-24
• WGK Germany: 3
• Hazardous Substances Data: 84793-24-8(Hazardous Substances Data)

Usage

Chemical Properties

White powder

Uses

N-[1-(S)-Ethoxycarbonyl-3-phenylpropyl]-L-alanine-N-carboxyanhydride is an impurity of Enalapril (E555250), an?antihypertensive and an angiotensin-converting enzyme (ACE) inhibitor.

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

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

Downstream Products

• 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 
• 852921-57-4 N-[1-(S)-carbethoxy-3-phenylpropyl]-(S)-alanyl-2R,3aS,7aR-octahydroindole-2-carboxylic acid 
• 87679-37-6 trandolapril 
• 928142-34-1 t-butyl-(4S)-3-[(2S)-2-[[(1S)-1-(ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1-methyl-2-oxo-4-imidazolidinecarboxylate hydrochloride 
• 98677-37-3 trandolapril benzyl ester 
• 87333-19-5 Ramipril 
• 103733-40-0 tert-butyl (S)-2-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-3-carboxylate 
• 89371-38-0 tert-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-ethoxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylate 
• 108428-39-3 N--L-alanyl>-L-proline tert butyl ester 
• 87269-88-3 2--L-alanyl>-(1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid benzylester 
• 83435-67-0 delapril hydrochloride 

Relevant articles and documents

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 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.