(2S)-1-[(2R)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-1-oxopropyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid

Base Information

• Chemical Name: (2S)-1-[(2R)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-1-oxopropyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid
• CAS No.: 87679-37-6
• Molecular Formula: C24H34N2O5
• Molecular Weight: 430.544
• Hs Code.: 2933995300
• NSC Number: 758939
• Wikidata: Q27165587
• ChEMBL ID: CHEMBL3039089
• Mol file: 87679-37-6.mol

Synonyms:Spectrum2_001249;Spectrum3_001061;Spectrum4_001206;Spectrum5_000646;BSPBio_002642;KBioGR_001612;SPECTRUM1505264;SPBio_001158;CHEMBL3039089;CHEBI:93846;KBio3_001862;HMS1922P13;Pharmakon1600-01505264;CCG-39132;NSC758939;NCGC00178557-01;NCGC00178557-02;AB01563054_01;BRD-A32505112-001-02-8;BRD-A32505112-001-03-6;Q27165587;(2S)-1-[(2R)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-1-oxopropyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid

Chemical Property of (2S)-1-[(2R)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-1-oxopropyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 1.55E-16mmHg at 25°C
• Melting Point: 122-123 °C
• Refractive Index: 1.549
• Boiling Point: 626 °C at 760 mmHg
• PKA: 3.15±0.20(Predicted)
• Flash Point: 332.4 °C
• PSA: 95.94000
• Density: 1.181 g/cm³
• LogP: 3.10210
• Storage Temp.: Room temp
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 430.24677219
• Heavy Atom Count: 31
• Complexity: 634

Purity/Quality:

Trandolapril ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2C3CCCCC3CC2C(=O)O
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@H](C)C(=O)N2[C@@H](CC3C2CCCC3)C(=O)O
• Description: Trandolapril is a new ACE inhibitor that is rapidly hydrolyzed, mainly in the liver, to its biologically active form, trandolaprilat. Compared with all other ACE inhibitors, trandolaprilat is reported to have the highest lipophilicity and the most prolonged ACE inhibitory activity. In hypertensive patients, trandolapril at a dose of 2 mg reduces blood pressure consistently throughout the 24 hour period after intake, making it one of the best once a day antihypertensive drugs. It has also been demonstrated to inhibit aortic atherosclerosis in the hyperlipidemic rabbit.
• Uses: Trandolapril has been used as an angiotensin-converting enzyme (ACE) inhibitor to study its effects on responsiveness of human retinal endothelial cells (HRECs) to vascular endothelial growth factor (VEGF). An antihypertensive. Angiotensin converting enzyme (ACE) inhibitor antibacterial
• Clinical Use: Angiotensin converting enzyme inhibitor: Hypertension Heat failure After myocardial infarction
• Drug interactions: Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect. Analgesics: antagonism of hypotensive effect and increased risk of renal impairment with NSAIDs; hyperkalaemia with ketorolac and other NSAIDs. Antihypertensives: increased risk of hyperkalaemia, hypotension and renal failure with ARBs and aliskiren. Bee venom extract: possible severe anaphylactoid reactions when used together. Ciclosporin: increased risk of hyperkalaemia and nephrotoxicity. Cytotoxics: increased risk of angioedema with everolimus. Diuretics: enhanced hypotensive effect; hyperkalaemia with potassium-sparing diuretics. ESAs: increased risk of hyperkalaemia; antagonism of hypotensive effect. Gold: flushing and hypotension with sodium aurothiomalate. Lithium: reduced excretion (possibility of enhanced lithium toxicity). Potassium salts: increased risk of hyperkalaemia. Tacrolimus: increased risk of hyperkalaemia and nephrotoxicity.

Technology Process of (2S)-1-[(2R)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-1-oxopropyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid

There total 24 articles about (2S)-1-[(2R)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]-1-oxopropyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

tert-butyl (2S,3aR,7aS)-1-(((S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl)-L-alanyl)octahydro-1H-indole-2-carboxylate → trandolapril (87679-37-6,80876-01-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 0.5h; Inert atmosphere;

DOI:10.1055/s-0037-1612306

Reference yield:

cis,syn-octahydro-1H-indole-2(S)-carboxylic acid, phenylmethylester (82717-90-6) + [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine (82717-96-2,122076-80-6) → trandolapril (87679-37-6,80876-01-3)

Guidance literature:

cis,syn-octahydro-1H-indole-2(S)-carboxylic acid, phenylmethylester; [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 20 - 25 ℃; for 3h;

With hydrogen; palladium 10% on activated carbon; In isopropyl alcohol; at 25 - 35 ℃; under 1471.14 - 2206.72 Torr;

With diethyl ether; for 0.0833333 - 0.166667h;

Reference yield:

cis,syn-octahydro-1H-indole-2(S)-carboxylic acid, phenylmethylester (82717-90-6) + [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine (82717-96-2,122076-80-6) → N-[1-(S)-carbethoxy-3-phenylpropyl]-(S)-alanyl-2R,3aS,7aR-octahydroindole-2-carboxylic acid (852921-57-4,80876-01-3) + trandolapril (87679-37-6,80876-01-3)

Guidance literature:

cis,syn-octahydro-1H-indole-2(S)-carboxylic acid, phenylmethylester; [1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine; With benzotriazol-1-ol; dicyclohexyl-carbodiimide; In dichloromethane; at 20 - 25 ℃; for 3h;

With hydrogen; palladium 10% on activated carbon; In isopropyl alcohol; at 25 - 35 ℃; under 1471.14 - 2206.72 Torr;

upstream raw materials:

[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine

rac-trans-octahydroindole-2-carboxylic acid

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

tert-butyl (S)-N-tert-butoxycarbonylpyroglutamate

Downstream raw materials:

[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF AMIDES OF N-[1-(S)-(ETHOXYCARBONYL)-3-PHENYLPROPYL]-L-ALANINE". Page/Page column 23. . Retrieved 2015/01/07.
• 2、 -. "Method for producing {n-[1-(s)-carbalkoxy-3-phenylpropyl]-s-alanyl-2s, 3ar, 7as-octahydroindole-2-carboxylic acid} compounds". . . Retrieved 2008/06/13.