(R)-Amlodipine

Base Information

• Chemical Name: (R)-Amlodipine
• CAS No.: 103129-81-3
• Molecular Formula: C20H25 Cl N2 O5
• Molecular Weight: 408.882
• UNII: YUH55G7ZTY
• DSSTox Substance ID: DTXSID90430938
• Nikkaji Number: J552.119J
• Wikidata: Q27124216
• Metabolomics Workbench ID: 58763
• Mol file: 103129-81-3.mol

Synonyms:(R)-Amlodipine;103129-81-3;(+)-Amlodipine;d-Amlodipine;(R)-(+)-Amlodipine;Amlodipine, (R)-;Amlodipine, (+)-;UNII-YUH55G7ZTY;YUH55G7ZTY;3,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester, (4R)-;3,5-Pyridinedicarboxylic acid, 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-, 3-ethyl 5-methyl ester, (R)-;06X;3-ethyl 5-methyl (4R)-2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate;(+) amlodipine;3-O-ethyl 5-O-methyl (4R)-2-(2-aminoethoxymethyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate;SCHEMBL912531;CHEBI:53795;DTXSID90430938;HTIQEAQVCYTUBX-QGZVFWFLSA-N;AKOS027446451;(4R)-2-[(2-Aminoethoxy)methyl]-4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic Acid 3-Ethyl 5-Methyl Ester;PD132985;E72658;J-000879;Q27124216;(R)-3-Ethyl 5-methyl 2-((2-aminoethoxy)methyl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3,5-dicarboxylate

Chemical Property of (R)-Amlodipine

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 101-103°C
• Refractive Index: 1.546
• Boiling Point: 527.161°C at 760 mmHg
• PKA: 8.97±0.10(Predicted)
• Flash Point: 272.617°C
• PSA: 162.63000
• Density: 1.228g/cm³
• LogP: 5.30950
• Storage Temp.: -20°C Freezer
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 10
• Exact Mass: 408.1451996
• Heavy Atom Count: 28
• Complexity: 647

Purity/Quality:

99% ^*data from raw suppliers

(R)-Amlodipine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(NC(=C(C1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
• Isomeric SMILES: CCOC(=O)C1=C(NC(=C([C@H]1C2=CC=CC=C2Cl)C(=O)OC)C)COCCN
• Uses: (R)-Enantiomer of Amlodipine (A633495). A dihydropyridine calcium channel blocker; activity resides mainly in the (-)-isomer. (R)-Enantiomer of Amlodipine. A dihydropyridine calcium channel blocker; activity resides mainly in the (-)-isomer.

Technology Process of (R)-Amlodipine

There total 12 articles about (R)-Amlodipine 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: 96.25%

L-Tartaric acid (87-69-4,138508-61-9) + 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (88150-42-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (S)-amlodipine-L-hemitartrate dimethylformamide solvate + (R)-amlodipine-L-hemitartrate dimethylformamide solvate + (R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (103129-81-3)

Guidance literature:

at 20 ℃; for 4.5h; Product distribution / selectivity;

Reference yield: 91.0%

→ (R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (103129-81-3)

Guidance literature:

Reference yield: 82.62%

L-Tartaric acid (87-69-4,138508-61-9) + 2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine (88150-42-9) + N,N-dimethyl-formamide (68-12-2,33513-42-7) → (S)-amlodipine-L-hemitartrate dimethylformamide solvate + (R)-2-[(2-aminoethoxy)methyl]4-(2-chlorophenyl)-1,4-dihydro-6-methyl-3,5-pyridinedicarboxylic acid 3-ethyl 5-methyl ester (103129-81-3)

Guidance literature:

In water; at 20 ℃; for 2 - 4.5h; Product distribution / selectivity;

upstream raw materials:

2-<(2-azidoethoxy)methyl>-4(R)-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-1,4-dihydropyridine

2-<(2-azidoethoxy)methyl>-4-(2-chlorophenyl)-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

(-)-2-<(2-azidoethoxy)methyl>-4-(2-chlorophenyl)-5-(methoxycarbonyl)-3-<(2(S)-methoxy-2-phenethoxy)carbonyl>-6-methyl-1,4-dihydropyridine

2-cyanoethyl 4-(2-azidoethoxy)-3-oxobutanoate

Downstream raw materials:

ramipril-amlodipine salt

amlodipine

2-[(2-aminoethoxy)methyl]-4-(2-chlorophenyl)-3-ethoxycarbonyl-5-methoxycarbonyl-6-methyl-1,4-dihydropyridine

2-(2-Amino-ethoxymethyl)-4-(2-chloro-phenyl)-6-methyl-pyridine-3,5-dicarboxylic acid 3-ethyl ester 5-methyl ester

Refernces

• 1、 Bánhegyi, Dorottya Fruzsina,Madarász, János,Pálovics, Emese,Szolcsányi, Dóra. "Enantiomeric separation of racemic amlodipine by sequential fractional crystallization through formation of diastereomeric salt solvates and co-crystals of solvate-like compounds with specific structure — A tandem resolution". . . Retrieved 2021/11/22.
• 2、 Kucerova, Gabriela,Kalikova, Kveta,Tesarova, Eva. "Enantioselective potential of polysaccharide-based chiral stationary phases in supercritical fluid chromatography". supporting information. p. 239 - 246. Retrieved 2017/05/29.