Orthohydroxyatorvastatin

Base Information

• Chemical Name: Orthohydroxyatorvastatin
• CAS No.: 214217-86-4
• Molecular Formula: C33H34FN2O6.Na.2H2O
• Molecular Weight: 574.649
• UNII: 5267B75F6S
• Nikkaji Number: J996.542D
• Wikidata: Q27088153
• Pharos Ligand ID: S299AQ1GZGMA
• ChEMBL ID: CHEMBL1565
• Mol file: 214217-86-4.mol

Synonyms:Orthohydroxyatorvastatin;o-Hydroxyatorvastatin;214217-86-4;5267B75F6S;BMS-243887;BMS 243887-01;PD 152873;UNII-5267B75F6S;(3R,5R)-7-(2-(4-fluorophenyl)-4-(2-hydroxyphenylcarbamoyl)-5-isopropyl-3-phenyl-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoic acid;(3R,5R)-7-[2-(4-fluorophenyl)-4-[(2-hydroxyphenyl)carbamoyl]-3-phenyl-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid;(3r,5r)-7-[2-(4-Fluorophenyl)-4-[(2-Hydroxyphenyl)carbamoyl]-5-(1-Methylethyl)-3-Phenyl-1h-Pyrrol-1-Yl]-3,5-Dihydroxyheptanoic Acid;D03TKT;CHEMBL1565;GTPL6705;SCHEMBL14105892;BDBM24426;Pyrrole Series 4 Compound, 13;PD-152873;Q27088153;(3R,5R)-7-[2-(4-fluorophenyl)-4-[(2-hydroxyphenyl)carbamoyl]-3-phenyl-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoic acid;1H-PYRROLE-1-HEPTANOIC ACID, 2-(4-FLUOROPHENYL)-.BETA.,.DELTA.-DIHYDROXY-4-(((2-HYDROXYPHENYL)AMINO)CARBONYL)-5-(1-METHYLETHYL)-3-PHENYL-, (.BETA.R,.DELTA.R)-;3HI

Chemical Property of Orthohydroxyatorvastatin

Chemical Property:

• Melting Point: 132-134°C
• Boiling Point: 741.9±60.0 °C(Predicted)
• PKA: 4.29±0.10(Predicted)
• PSA: 153.31000
• Density: 1.27
• LogP: 4.62890
• Storage Temp.: -20°C Freezer
• Solubility.: Methanol (Slightly)
• XLogP3: 4.6
• Hydrogen Bond Donor Count: 5
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 574.24791500
• Heavy Atom Count: 42
• Complexity: 862

Purity/Quality:

98%Min ^*data from raw suppliers

ortho-HydroxyAtorvastatin ^*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)O)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4O
• Isomeric SMILES: CC(C)C1=C(C(=C(N1CC[C@H](C[C@H](CC(=O)O)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4O
• Uses: A deuterated metabolite of Atorvastin, a selective, competitive HMG-CoA reductase inhibitor. Atorvastin is the only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in patients with hypercholester

Technology Process of Orthohydroxyatorvastatin

There total 10 articles about Orthohydroxyatorvastatin 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:

atorvastatin (134523-00-5,110862-48-1) → p-Hydroxyatorvastatin (214217-88-6) + o-Hydroxyatorvastatin (214217-86-4)

Guidance literature:

With chimera No_.17A₁V₂ derived from CYP₁₀₂A₁ mutant; In aq. phosphate buffer; dimethyl sulfoxide; Reagent/catalyst; Catalytic behavior; Enzymatic reaction;

Reference yield:

(3R,5R)-7-[2-(4-Fluoro-phenyl)-4-(2-hydroxy-phenylcarbamoyl)-5-isopropyl-3-phenyl-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid tert-butyl ester (1346599-89-0) → o-Hydroxyatorvastatin (214217-86-4)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1002/(SICI)1099-1344(20000315)43:3<261::AID-JLCR312>3.0.CO;2-T

Reference yield:

o-(benzyloxy)aniline (20012-63-9) → o-Hydroxyatorvastatin (214217-86-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 76 percent / toluene / Heating

2: β-alanine; glacial acetic acid / hexane / Heating

3: 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromide; triethylamine / ethanol / Heating

4: pivalic acid / tetrahydrofuran; toluene; heptane / Heating

5: 35 percent / hydrogen; acetic acid / palladium on carbon / ethyl acetate

6: HCl / tetrahydrofuran; H₂O / 20 °C

7: sodium hydroxide / H₂O; tetrahydrofuran / 20 °C

With hydrogenchloride; sodium hydroxide; hydrogen; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; acetic acid; triethylamine; 3-amino propanoic acid; Trimethylacetic acid; palladium on activated charcoal; In tetrahydrofuran; ethanol; hexane; n-heptane; water; ethyl acetate; toluene; 1: Acylation / 2: Condensation / 3: Addition / 4: Cycloaddition / 5: Hydrogenolysis / 6: Hydrolysis / 7: Hydrolysis;

DOI:10.1002/(SICI)1099-1344(20000315)43:3<261::AID-JLCR312>3.0.CO;2-T

upstream raw materials:

(3R,5R)-7-[2-(4-Fluoro-phenyl)-4-(2-hydroxy-phenylcarbamoyl)-5-isopropyl-3-phenyl-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid tert-butyl ester

o-(benzyloxy)aniline

2-benzyloxynitrobenzene

N-(2-(benzyloxy)phenyl)-4-methyl-3-oxopentanamide

Downstream raw materials:

o-Hydroxyatorvastatin lactone

Refernces

• 1、 -. "NOVEL METHOD FOR PREPARING METABOLITES OF ATORVASTATIN USING BACTERIAL CYTOCHROME P450 AND COMPOSITION THEREFOR". Paragraph 65-71; 96-127. . Retrieved 2013/06/05.
• 2、 Chen, Bang-Chi,Sundeen, Joseph E.,Guo, Peng,Bednarz, Mark S.,Hangeland, Jon J.,Ahmed, Syed Z.,Jemal, Mohammed. "Synthesis of deuterium-labeled atorvastatin and its metabolites for use as internal standards in a LC/MS/MS method developed for quantitation of the drug and its metabolites in human serum". . p. 261 - 270. Retrieved 2007/10/03.