(S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid monomethyl ester

Base Information

• Chemical Name: (S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid monomethyl ester
• CAS No.: 76093-34-0
• Molecular Formula: C16H16 N2 O6
• Molecular Weight: 332.313
• DSSTox Substance ID: DTXSID80353703
• Nikkaji Number: J806.749J
• Wikidata: Q82131427
• Mol file: 76093-34-0.mol

Synonyms:76093-34-0;(S)-(+)-1,4-DIHYDRO-2,6-DIMETHYL-4-(3-NITROPHENYL)-3,5-PYRIDINEDICARBOXYLIC ACID MONOMETHYL ESTER;(4S)-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid;3,5-Pyridinedicarboxylicacid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-methyl ester, (4S)-;(S)-5-(Methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid;(4s)-5-(methoxycarbonyl)-2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid;SCHEMBL4654954;DTXSID80353703;AKOS030242947;CS-0130762;(S)-(+)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-3-pyridinecarboxylic acid

Chemical Property of (S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid monomethyl ester

Chemical Property:

• Vapor Pressure: 5.1E-11mmHg at 25°C
• Melting Point: 200 °C
• Refractive Index: 1.587
• Boiling Point: 505°C at 760 mmHg
• PKA: 1.66±0.70(Predicted)
• Flash Point: 259.2°C
• PSA: 121.45000
• Density: 1.345g/cm³
• LogP: 2.93920
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 332.10083623
• Heavy Atom Count: 24
• Complexity: 631

Purity/Quality:

99.3% ^*data from raw suppliers

(S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylicAcidMonomethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=C(C(C(=C(N1)C)C(=O)OC)C2=CC(=CC=C2)[N+](=O)[O-])C(=O)O
• Isomeric SMILES: CC1=C([C@@H](C(=C(N1)C)C(=O)OC)C2=CC(=CC=C2)[N+](=O)[O-])C(=O)O
• Uses: 1,4-Dihydropyridine derivative used in the prevention and therapy of atherosclerotic degradation of arterial walls

Technology Process of (S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid monomethyl ester

There total 23 articles about (S)-(+)-1,4-Dihydro-2,6-dimethyl-4-(3-nitrophenyl)-3,5-pyridinedicarboxylic acid monomethyl ester 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: 84.0%

C16H16N2O6*C19H22N2O (134028-03-8) → (+)-(S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid (76093-34-0)

Guidance literature:

With hydrogenchloride; In water; ethyl acetate; Cooling;

DOI:10.1016/j.bmcl.2009.12.104

Reference yield: 73.0%

3-allyl 5-methyl (4R)-1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)pyridine-3,5-dicarboxylate → (+)-(S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid (76093-34-0)

Guidance literature:

With palladium diacetate; formic acid; triethylamine; triphenylphosphine; In tetrahydrofuran; for 0.25h; Heating;

DOI:10.3987/COM-94-S(B)51

Reference yield: 48.0%

(4S)-1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylic acid (76093-32-8) → (+)-(S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylic acid (76093-34-0)

Guidance literature:

With hydrogenchloride; In acetone; Ambient temperature;

DOI:10.1248/cpb.37.2225

upstream raw materials:

(4S)-1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-3-pyridinecarboxylic acid

2-cyanoethyl (R)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-3-pyridinecarboxylate

(R)-2,6-Dimethyl-4-(3-nitro-phenyl)-1,4-dihydro-pyridine-3,5-dicarboxylic acid 3-(2-methanesulfonyl-ethyl) ester 5-methyl ester

1-ethoxymethyl-1,4-dihydro-5-methoxycarbonyl-2,6-dimethyl-4-(3-nitrophenyl)-pyridine-3-carboxylic acid

Downstream raw materials:

3-Iodopropyl (4S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)pyridine-3-carboxylate

3-(3-pyridyl)propyl (4S)-1,4-dihydro-2,6-dimethyl-5-methoxycarbonyl-4-(3-nitrophenyl)-pyridine-3-carboxylate

(4R)-3-(1-benzyl-3-methylpyrrolidin-3-yl) 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate hydrochloride

(3R)-1-benzyl-3-pyrrolidinyl methyl (4S)-2,6-dimethyl-4-(m-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate

Refernces

• 1、 -. "Process for synthesis of hydrochloric acid ramiah of lercanidipine (by machine translation)". . . Retrieved 2016/12/01.
• 2、 -. "1,4-DIHYDROPYRIDINE -3,5-DICARBOXYLATE DERIVATIVES, PREPARATION METHODS AND USES THEREOF". . . Retrieved 2014/03/25.