(6-{2-[2-(4-Fluoro-phenyl)-4-(4-hydroxy-phenylcarbamoyl)-5-isopropyl-3-phenyl-pyrrol-1-yl]-ethyl}-2,2-dimethyl-[1,3]-dioxane-4-yl)-acetic Acid, tert-B

Base Information

• Chemical Name: (6-{2-[2-(4-Fluoro-phenyl)-4-(4-hydroxy-phenylcarbamoyl)-5-isopropyl-3-phenyl-pyrrol-1-yl]-ethyl}-2,2-dimethyl-[1,3]-dioxane-4-yl)-acetic Acid, tert-B
• CAS No.: 265989-36-4
• Molecular Formula: C40H47FN2O6
• Molecular Weight: 670.821
• DSSTox Substance ID: DTXSID90441948
• Wikidata: Q72476059
• Mol file: 265989-36-4.mol

Synonyms:265989-36-4;(6-{2-[2-(4-Fluoro-phenyl)-4-(4-hydroxy-phenylcarbamoyl)-5-isopropyl-3-phenyl-pyrrol-1-yl]-ethyl}-2,2-dimethyl-[1,3]-dioxane-4-yl)-acetic Acid, tert-B;Tert-butyl 2-[(4R,6R)-6-[2-[2-(4-fluorophenyl)-4-[(4-hydroxyphenyl)carbamoyl]-3-phenyl-5-propan-2-ylpyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate;1,3-Dioxane-4-acetic acid, 6-[2-[2-(4-fluorophenyl)-4-[[(4-hydroxyphenyl)amino]carbonyl]-5-(1-methylethyl)-3-phenyl-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R,6R)-;tert-Butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-4-((4-hydroxyphenyl)carbamoyl)-5-isopropyl-3-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;tert-butyl 2-[(4R,6R)-6-{2-[2-(4-fluorophenyl)-4-[(4-hydroxyphenyl)carbamoyl]-3-phenyl-5-(propan-2-yl)-1H-pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate;SCHEMBL7683385;DTXSID90441948;AKOS015901512;AC-7931;tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-4-(4-hydroxyphenylcarbamoyl)-5-isopropyl-3-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;4-Hydroxy Atorvastatin Acetonide tert-Butyl Ester;tert-Butyl [(4R,6R)-6-{2-[2-(4-fluorophenyl)-4-[(4-hydroxyphenyl)carbamoyl]-3-phenyl-5-(propan-2-yl)-1H-pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate;tert-butyl 2-[(4R, 6R)-6-[2-[2-(4-fluorophenyl)-4-[(4-hydroxyphenyl)carbamoyl]-3-phenyl-5-propan-2-ylpyrrol-1-yl]ethyl]-2, 2-dimethyl-1, 3-dioxan-4-yl]acetate

Chemical Property of (6-{2-[2-(4-Fluoro-phenyl)-4-(4-hydroxy-phenylcarbamoyl)-5-isopropyl-3-phenyl-pyrrol-1-yl]-ethyl}-2,2-dimethyl-[1,3]-dioxane-4-yl)-acetic Acid, tert-B

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 707.815°C at 760 mmHg
• PKA: 10.00±0.26(Predicted)
• Flash Point: 381.873°C
• PSA: 99.02000
• Density: 1.184g/cm³
• LogP: 9.14760
• Solubility.: Acetone, Chloroform, Dichloromethane, Ethyl Acetate
• XLogP3: 7.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 12
• Exact Mass: 670.34181539
• Heavy Atom Count: 49
• Complexity: 1070

Purity/Quality:

98%min ^*data from raw suppliers

4-HydroxyAtorvastatinAcetonidetert-ButylEster ^*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(OC(O2)(C)C)CC(=O)OC(C)(C)C)C3=CC=C(C=C3)F)C4=CC=CC=C4)C(=O)NC5=CC=C(C=C5)O
• Isomeric SMILES: CC(C)C1=C(C(=C(N1CC[C@@H]2C[C@@H](OC(O2)(C)C)CC(=O)OC(C)(C)C)C3=CC=C(C=C3)F)C4=CC=CC=C4)C(=O)NC5=CC=C(C=C5)O
• Uses: An intermediate of the 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.

Technology Process of (6-{2-[2-(4-Fluoro-phenyl)-4-(4-hydroxy-phenylcarbamoyl)-5-isopropyl-3-phenyl-pyrrol-1-yl]-ethyl}-2,2-dimethyl-[1,3]-dioxane-4-yl)-acetic Acid, tert-B

There total 6 articles about (6-{2-[2-(4-Fluoro-phenyl)-4-(4-hydroxy-phenylcarbamoyl)-5-isopropyl-3-phenyl-pyrrol-1-yl]-ethyl}-2,2-dimethyl-[1,3]-dioxane-4-yl)-acetic Acid, tert-B 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: 89.8%

tert-butyl 2-((4R,6R)-6-(2-(3-((4-(benzyloxy)phenyl)carbamoyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (163217-68-3) → tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-4-((4-hydroxyphenyl)carbamoyl)-5-isopropyl-3-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (265989-36-4)

Guidance literature:

With palladium on activated charcoal; hydrogen; In methanol; at 50 ℃; for 20h; under 2585.81 Torr;

Reference yield:

N-(4-(benzyloxy)phenyl)-4-methyl-3-oxopentanamide (265989-30-8) → tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-4-((4-hydroxyphenyl)carbamoyl)-5-isopropyl-3-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (265989-36-4)

Guidance literature:

Multi-step reaction with 4 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: 85 percent / hydrogen; acetic acid / palladium on carbon / ethyl acetate / 34 h / 2585.74 Torr

With 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; ethyl acetate; toluene; 1: Condensation / 2: Addition / 3: Cycloaddition / 4: Hydrogenolysis;

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

Reference yield:

p-benzyloxyaniline (6373-46-2) → tert-butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-4-((4-hydroxyphenyl)carbamoyl)-5-isopropyl-3-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate (265989-36-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 82 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: 85 percent / hydrogen; acetic acid / palladium on carbon / ethyl acetate / 34 h / 2585.74 Torr

With 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; ethyl acetate; toluene; 1: Acylation / 2: Condensation / 3: Addition / 4: Cycloaddition / 5: Hydrogenolysis;

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

upstream raw materials:

tert-butyl 2-((4R,6R)-6-(2-(3-((4-(benzyloxy)phenyl)carbamoyl)-5-(4-fluorophenyl)-2-isopropyl-4-phenyl-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate

p-benzyloxyaniline

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

N-(4-(benzyloxy)phenyl)-2-(2-(4-fluorophenyl)-2-oxo-1-phenylethyl)-4-methyl-3-oxopentanamide

Downstream raw materials:

C₄₆H₅₇FN₂O₈

p-Hydroxyatorvastatin lactone

p-Hydroxyatorvastatin

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.