O-Hydroxyatorvastatin lactone

Base Information

• Chemical Name: O-Hydroxyatorvastatin lactone
• CAS No.: 163217-74-1
• Molecular Formula: C₃₃H₃₃FN₂O₅
• Molecular Weight: 556.634
• UNII: N8OH05250C
• DSSTox Substance ID: DTXSID50167536
• Nikkaji Number: J1.137.567G
• Wikidata: Q27284712
• Mol file: 163217-74-1.mol

Synonyms:2-Hydroxy Atorvastatin Lactone;163217-74-1;O-HYDROXYATORVASTATIN LACTONE;O-Hydroxy atorvastatin lactone;Orthohydroxyatorvastatin lactone;Ortho-Hydroxy Atorvastatin Lactone;UNII-N8OH05250C;N8OH05250C;5-(4-Fluorophenyl)-1-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)-ethyl)-N-(2-hydroxyphenyl)-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxamide;5-(4-fluorophenyl)-1-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-N-(2-hydroxyphenyl)-4-phenyl-2-propan-2-ylpyrrole-3-carboxamide;(2R-Trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N-(2-hydroxyphenyl)-4-phenyl-1-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-1H-pyrrole-3-carboxamide;1H-Pyrrole-3-carboxamide, 5-(4-fluorophenyl)-N-(2-hydroxyphenyl)-2-(1-methylethyl)-4-phenyl-1-(2-((2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-;1H-Pyrrole-3-carboxamide, 5-(4-fluorophenyl)-N-(2-hydroxyphenyl)-2-(1-methylethyl)-4-phenyl-1-(2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl)-, (2R-trans)-;1H-Pyrrole-3-carboxamide, 5-(4-fluorophenyl)-N-(2-hydroxyphenyl)-2-(1-methylethyl)-4-phenyl-1-[2-[(2R,4R)-tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl]ethyl]-;5-(4-fluorophenyl)-1-(2-((2R,4R)-4-hydroxy-6-oxotetrahydro-2H-pyran-2-yl)ethyl)-N-(2-hydroxyphenyl)-2-isopropyl-4-phenyl-1H-pyrrole-3-carboxamide;5-(4-fluorophenyl)-1-{2-[(2r,4r)-4-hydroxy-6-oxotetrahydro-2h-pyran-2-yl]ethyl}-n-(2-hydroxyphenyl)-2-isopropyl-4-phenyl-1h-pyrrole-3-carboxamide;Atorvastatin 2-Hydroxy Lactone;SCHEMBL5605044;DTXSID50167536;CHEBI:183888;AKOS030241919;CS-O-14406;HY-136346;CS-0128382;J-010021;Q27284712;5-(4-luorophenyl)-1-[2-[(2R,4R)-4-hydroxy-6-oxooxan-2-yl]ethyl]-N-(2-hydroxyphenyl)-4-phenyl-2-propan-2-ylpyrrole-3-carboxamide

Chemical Property of O-Hydroxyatorvastatin lactone

Chemical Property:

• Melting Point: 110-112°C
• PSA: 100.79000
• LogP: 6.57210
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• XLogP3: 5.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 8
• Exact Mass: 556.23735032
• Heavy Atom Count: 41
• Complexity: 874

Purity/Quality:

99% ^*data from raw suppliers

o-Hydroxy Atorvastatin Lactone ^*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(N1CCC2CC(CC(=O)O2)O)C3=CC=C(C=C3)F)C4=CC=CC=C4)C(=O)NC5=CC=CC=C5O
• Isomeric SMILES: CC(C)C1=C(C(=C(N1CC[C@@H]2C[C@H](CC(=O)O2)O)C3=CC=C(C=C3)F)C4=CC=CC=C4)C(=O)NC5=CC=CC=C5O
• Uses: A 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 hypercholesterolemia A metabolite of Atorvastatin, a selective, competitive HMG-CoA reductase inhibitor. Atorvastatin is the only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in patients with hypercholesterolemia. Atorvastatin metabolite

Technology Process of O-Hydroxyatorvastatin lactone

There total 14 articles about O-Hydroxyatorvastatin lactone 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:

(2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N-(4-benzyloxyphenyl)-4-phenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo-2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide → o-Hydroxyatorvastatin lactone (163217-74-1)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; ethyl acetate; isopropyl alcohol; at 25 - 45 ℃; for 12h; under 3750.38 - 4125.41 Torr;

Reference yield:

o-(benzyloxy)aniline (20012-63-9) → o-Hydroxyatorvastatin lactone (163217-74-1)

Guidance literature:

Multi-step reaction with 8 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

8: trifluoroacetic acid / ethyl acetate / Heating

With hydrogenchloride; sodium hydroxide; hydrogen; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; acetic acid; triethylamine; trifluoroacetic acid; 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 / 8: Cyclization;

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

Reference yield:

N-(2-(benzyloxy)phenyl)-4-methyl-3-oxopentanamide (265989-31-9) → o-Hydroxyatorvastatin lactone (163217-74-1)

Guidance literature:

Multi-step reaction with 7 steps

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

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

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

4: 35 percent / hydrogen; acetic acid / palladium on carbon / ethyl acetate

5: HCl / tetrahydrofuran; H₂O / 20 °C

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

7: trifluoroacetic acid / ethyl acetate / Heating

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

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

upstream raw materials:

o-Hydroxyatorvastatin

o-(benzyloxy)aniline

2-benzyloxynitrobenzene

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

Refernces

• 1、 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.