(2R,3aR,6aR)-1-((2S)-2-(((1S)-1-(Ethoxycarbonyl)-3-phenylpropyl)amino)propanoyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acid

Base Information

• Chemical Name: (2R,3aR,6aR)-1-((2S)-2-(((1S)-1-(Ethoxycarbonyl)-3-phenylpropyl)amino)propanoyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acid
• CAS No.: 129939-63-5
• Molecular Formula: C₂₃H₃₂N₂O₅
• Molecular Weight: 416.517
• UNII: MFY4AI76OW
• Nikkaji Number: J1.380.336F
• Wikidata: Q27284008
• Mol file: 129939-63-5.mol

Synonyms:129939-63-5;Ramipril impurity N [EP];Ramipril isomer, (S,S,R,R,R)-;MFY4AI76OW;(2R,3aR,6aR)-Ramipril;(2R,3aR,6aR)-1-((2S)-2-(((1S)-1-(Ethoxycarbonyl)-3-phenylpropyl)amino)propanoyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acid;(+)-Cyclopenta(b)pyrrole-2-carboxylic acid, 1-((2S)-2-(((1S)-1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydro-, (2R,3aR,6aR)-;(2R,3aR,6aR)-1-[(2S)-2-[[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino]propanoyl]-3,3a,4,5,6,6a-hexahydro-2H-cyclopenta[b]pyrrole-2-carboxylic acid;Cyclopenta(b)pyrrole-2-carboxylic acid, 1-((2S)-2-(((1S)-1-(ethoxycarbonyl)-3-phenylpropyl)amino)-1-oxopropyl)octahydro-, (2R,3aR,6aR)-;(2R,3aR,6aR)-1-((S)-2-(((S)-1-Ethoxy-1-oxo-4-phenylbutan-2-yl)amino)propanoyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid;UNII-MFY4AI76OW;SCHEMBL3533199;RAMIPRIL IMPURITY N [EP IMPURITY];Q27284008

Chemical Property of (2R,3aR,6aR)-1-((2S)-2-(((1S)-1-(Ethoxycarbonyl)-3-phenylpropyl)amino)propanoyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acid

Chemical Property:

• Melting Point: 40 - 50°C
• Storage Temp.: -20°C Freezer, Under inert atmosphere
• Solubility.: Acetonitrile (Slightly), Methanol (Slightly)
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 416.23112213
• Heavy Atom Count: 30
• Complexity: 619

Purity/Quality:

> 95% ^*data from raw suppliers

(2R,3aR,6aR)-Ramipril ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2C3CCCC3CC2C(=O)O
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2[C@@H]3CCC[C@@H]3C[C@@H]2C(=O)O
• Uses: An isomer of the angiotensin-converting enzyme (ACE) inhibitor Ramipril (R111000). Ramipril impurity N. (2R,3aR,6aR)-Ramipril (Ramipril EP Impurity N) is an isomer of the angiotensin-converting enzyme (ACE) inhibitor Ramipril (R111000). Ramipril impurity N.

Technology Process of (2R,3aR,6aR)-1-((2S)-2-(((1S)-1-(Ethoxycarbonyl)-3-phenylpropyl)amino)propanoyl)octahydrocyclopenta(b)pyrrole-2-carboxylic acid

There total 1 articles about (2R,3aR,6aR)-1-((2S)-2-(((1S)-1-(Ethoxycarbonyl)-3-phenylpropyl)amino)propanoyl)octahydrocyclopenta(b)pyrrole-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:

(1RS,3RS,5RS)-2-Azabicyclo<3.3.0>octan-3-carbonsaeure-hydrochlorid (87269-86-1,87758-19-8,93779-30-7,94062-51-8,96893-64-0,135214-81-2) + N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride (84793-24-8) → ramipril (129939-63-5,104195-90-6,1246253-05-3) + Ramipril (87333-19-5,104195-90-6,1246253-05-3)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃;

Reference yield:

ramipril (129939-63-5,104195-90-6,1246253-05-3) + 0.67Zn(2+)*0.33Al(3+)*2OH(1-)*0.33NO3(1-)*0.60H2O=[Zn0.67Al0.33(OH)2][NO3]0.33*0.60H2O → [Zn0.68Al0.32(OH)2](ramipril(-1H))0.219(C(00)O3)51*0.65H2O

Guidance literature:

With NaOH; In water; pH of aq. soln. of ramipril adjusted to at pH 5 by addn. of aq. NaOH; soln. added to aq. suspn. of Zn/Al layered double hydroxide; mixt. stirredmagnetically at room temp. under N2 atm. for 3 d; solid filtered off; washed with H2O until pH of 7; dried under vac. (N2 atm.) at room temp. for 48 h;

DOI:10.1016/j.jssc.2008.06.009

upstream raw materials:

(1RS,3RS,5RS)-2-Azabicyclo<3.3.0>octan-3-carbonsaeure-hydrochlorid

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