Atorvastatin Methyl Ester

Base Information

• Chemical Name: Atorvastatin Methyl Ester
• CAS No.: 345891-62-5
• Molecular Formula: C34H37FN2O5
• Molecular Weight: 572.677
• Hs Code.: 2933990090
• UNII: 2YR32CX5GQ
• DSSTox Substance ID: DTXSID40435534
• Nikkaji Number: J1.511.022H
• Wikidata: Q82250550
• ChEMBL ID: CHEMBL3754604
• Mol file: 345891-62-5.mol

Synonyms:Atorvastatin Methyl Ester;345891-62-5;(3R,5R)-Methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate;2YR32CX5GQ;methyl (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoate;Methyl (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate;(3R,5R)-methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate;(betaR,deltaR)-2-(4-Fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-Pyrrole-1-heptanoic acid methyl ester;Atorvastatin Calcium Impurity K;Atorvastatin Impurity K;UNII-2YR32CX5GQ;ATORVASTATIN IMPURITY 9;CHEMBL3754604;SCHEMBL12553314;DTXSID40435534;IRKGCTGBOBRSMG-VSGBNLITSA-N;AKOS016007755;HY-135376;CS-0112184;J-019663;(?R,?R)-2-(4-Fluorophenyl)-?,?-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic Acid Methyl Ester;1H-PYRROLE-1-HEPTANOIC ACID, 2-(4-FLUOROPHENYL)-.BETA.,.DELTA.-DIHYDROXY-5-(1-METHYLETHYL)-3-PHENYL-4-((PHENYLAMINO)CARBONYL)-, METHYL ESTER, (.BETA.R,.DELTA.R)-;1H-Pyrrole-1-heptanoic acid, 2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-, methyl ester, (betaR,deltaR)-;METHYL (.BETA.R,.DELTA.R)-2-(4-FLUOROPHENYL)-.BETA.,.DELTA.-DIHYDROXY-5-(1-METHYLETHYL)-3-PHENYL-4-((PHENYLAMINO)CARBONYL)-1H-PYRROLE-1-HEPTANOATE;Methyl (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate;Methyl (betaR,deltaR)-2-(4-fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrole-1-heptanoate

Chemical Property of Atorvastatin Methyl Ester

Chemical Property:

• Melting Point: 58-60°C
• Boiling Point: 703.7±60.0 °C(Predicted)
• PKA: 13.57±0.70(Predicted)
• PSA: 100.79000
• Density: 1.20±0.1 g/cm3(Predicted)
• LogP: 6.47500
• Storage Temp.: -20?C Freezer
• Solubility.: Acetonitrile (Slightly), Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 5.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 13
• Exact Mass: 572.26865045
• Heavy Atom Count: 42
• Complexity: 838

Purity/Quality:

99.9% ^*data from raw suppliers

AtorvastatinMethylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)C1=C(C(=C(N1CCC(CC(CC(=O)OC)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4
• Isomeric SMILES: CC(C)C1=C(C(=C(N1CC[C@H](C[C@H](CC(=O)OC)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4
• Uses: Atorvastatin impurity. Atorvastatin Methyl Ester Atorvastatin

Technology Process of Atorvastatin Methyl Ester

There total 9 articles about Atorvastatin Methyl 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: 94.0%

methyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (1353049-81-6) → (3R,5R)-methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate (345891-62-5)

Guidance literature:

With hydrogenchloride; In methanol; water; at 20 ℃; for 6h;

DOI:10.1021/jo402829b

Reference yield: 90.0%

methanol (67-56-1) + lipitor (134523-03-8) → (3R,5R)-methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate (345891-62-5)

Guidance literature:

With sulfuric acid; at 0 - 20 ℃; for 2.5h;

DOI:10.1016/j.bmcl.2015.12.069

Reference yield: 88.0%

methanol (67-56-1) + atorvastatin sodium (134523-01-6) → (3R,5R)-methyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate (345891-62-5)

Guidance literature:

With sulfuric acid; at 0 - 20 ℃; for 2.58333h;

DOI:10.1016/j.bioorg.2019.01.007

upstream raw materials:

methanol

atorvastatin

methyl 2-(6-(cyanomethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

methyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

Downstream raw materials:

(2E,5S)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]-5-hydroxyhept-2-enoic acid

atorvastatin

lipitor

benzyl (3R,5R)-7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate

Refernces

• 1、 Wang, Xin,Chong, Shuyi,Lin, Huiyun,Yan, Zhiqiang,Huang, Fengyu,Zeng, Zhiping,Zhang, Xiaokun,Su, Ying. "Discovery of atorvastatin as a tetramer stabilizer of nuclear receptor RXRα through structure-based virtual screening". . p. 413 - 419. Retrieved 2019/01/23.
• 2、 Chen, Xiaofei,Xiong, Fangjun,Chen, Wenxue,He, Qiuqin,Chen, Fener. "Asymmetric synthesis of the HMG-CoA reductase inhibitor atorvastatin calcium: An organocatalytic anhydride desymmetrization and cyanide-free side chain elongation approach". . p. 2723 - 2728. Retrieved 2014/04/17.