Atorvastatin Acetonide tert-Butyl Ester

Base Information

• Chemical Name: Atorvastatin Acetonide tert-Butyl Ester
• CAS No.: 125971-95-1
• Molecular Formula: C40H47FN2O5
• Molecular Weight: 654.822
• Hs Code.: 29349990
• European Community (EC) Number: 603-106-0,700-258-0
• UNII: 0PTA8HGH1F
• DSSTox Substance ID: DTXSID70436296
• Nikkaji Number: J3.152.684A
• Mol file: 125971-95-1.mol

Synonyms:125971-95-1;Atorvastatin Acetonide tert-Butyl Ester;tert-Butyl (4R,6R)-2-[[[6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate;0PTA8HGH1F;tert-Butyl 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;UNII-0PTA8HGH1F;tert-Butyl (4R,6R)-2-[6-[2-[2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate;1,3-Dioxane-4-acetic acid, 6-[2-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R,6R)-;tert-butyl 2-[(4R,6R)-6-[2-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate;EC 700-258-0;(4R,6R)-6-[2-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-Dioxane-4-acetic acid 1,1-dimethylethyl ester;(4R,6R)-6-(2-(2-(4-Fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxane-4-acetic acid 1,1-dimethylethyl ester;1,3-Dioxane-4-acetic acid, 6-(2-(2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-, 1,1-dimethylethyl ester, (4R,6R)-;1001659-85-3;MFCD04039904;1,1-Dimethylethyl 6-(2-(2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-((phenylamino)carbonyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-(4R,6R)-1,3-dioxane-4-acetate;1,1-dimethylethyl 6-[2-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-(4R,6R)-1,3-dioxane-4-acetate;tert-Butyl ((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;tert-butyl (4r,6r)-2-(((6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;tert-butyl [(4R,6R)-6-{2-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxan-4-yl]acetate;SCHEMBL583215;C40H47FN2O5;DTXSID70436296;tert-Butyl 2-((4R,6R)-6-(2-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenyl-caramoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)acetate;AKOS015900092;AM90283;AC-15555;DS-13827;tert-Butyl (4R,6R)-6-[2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1-pyrrolyl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate;HY-135380;B3690;CS-0112186;T70179;A805449;J-005310;ATORVASTATIN CALCIUM IMPURITY I [EP IMPURITY];(4R,6R)-6-[2-[2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrole-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetic acid tert-butyl ester;(4R-Cis)-1,1-dimethylethyl 6-[2[2-(4-fluoro-phenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino) -carbonyl]-1H-pyrrol-1-yl]ethyl]2,2-dimethyl-1,3-dioxane-4-acetate;(4R-cis)-1,1-dimethylethyl 6-[2[2-(4-fluoro-phenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)-carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate;(4R-cis)-1,1-dimethylethyl 6-[2[2-(4-fluorophenyl)-5-(1-methyl-ethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate;(4R-cis)-1,1-dimethylethyl 6-[2[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H -pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate;(4R-cis)-1,1-dimethylethyl 6-[2[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate;(4R-cis)-1,1-dimethylethyl 6-[2[2-(4fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl] ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate;(4r-cis)-1,1-Dimethylethyl-6-[2-(4-fluorophenyl)-5-(1-isopropyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate;(4r-cis)-6-[2-[3-phenyl-4-(phenylcarbamoyl)-2-(4-fluorophenyl)-5-(1-methylethyl)-pyrrol-1-yl]-ethyl]-2,2-dimethyl-[1,3]-dioxane-4-yl-acetic acid tert-butyl ester;(4R-cis)-6-[2-[3-phenyl-4-(phenylcarbamoyl)-2-(4-fluorophenyl)-5-(1-methylethyl)-pyrrol-1-yl]-ethyl]-2,2-dimethyl-[1,3]-dioxane-4-yl-acetic acid tertiary butyl ester;(6-{2-[3-(4-Phenylcarbamoyl)-5-(4-fluoro-phenyl)-2-isopropyl-4-phenyl-d5-pyrrol-1-yl]-ethyl}-2,2-dimethyl-[1,3]-dioxane-4-yl)-acetic acid,tert-butyl ester;(R-cis)-1,1dimethylethyl 6-[2[2-(4-fluorophenyl)-5-(1-methyl-ethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate;1,1-DIMETHYLETHYL (4R,6R)-6-(2-(2-(4-FLUOROPHENYL)-5-(1-METHYLETHYL)-3-PHENYL-4-((PHENYLAMINO)CARBONYL)-1H-PYRROL-1-YL)ETHYL)-2,2-DIMETHYL-1,3-DIOXANE-4-ACETATE;1,1-Dimethylethyl (4R-cis)-6-[2-[2-(4-Fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1-H-pyrrol-1-yl]ethyl]-2,2-di-methyl-1,3-dioxane-4-acetate;Atorvastatin Related Compound I;Atorvastatin Calcium Impurity I;Atorvastatin Impurity I;t-Butyl(4R,6R)-2-[6-[2-[2-(4-F-Ph)-5-isoprop-3-Ph-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-di-Me-1,3-dioxan-4-yl]acetate;98%;TERT-BUTYL ((4R,6R)-6-(2-(3-(ANILINOCARBONYL)-5-(4-FLUOROPHENYL)-2-ISOPROPYL-4-PHENYL-1H-PYRROL-1-YL)ETHYL)-2,2-DIMETHYL-1,3-DIOXAN-4-YL)ACETATE;TERT-BUTYL ((4R,6R)-6-(2-(3-(ANILINOCARBONYL)-5-(4-FLUOROPHENYL)-2-ISOPROPYL-4-PHENYL-1H-PYRROL-1-YL)ETHYL)-2,2-DIMETHYL-1,3-DIOXAN-4-YL)ACETATE, (+)-;tert-Butyl (4R,6R)-2-[[[6-(2-4-fluorophenyl)-5-isopropyl-3-phenyl-4- (phenylcarbamoyl)pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate;tert-Butyl (4R,6R)-6-[2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1-pyrrolyl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate, 97%;tert-Butyl [(4R,6R)-6-{2-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-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)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)ethyl)-2,2-dimethyl-1,3-dioxan-4-yl)

Chemical Property of Atorvastatin Acetonide tert-Butyl Ester

Chemical Property:

• Melting Point: 144-148 °C
• Boiling Point: 678.035 °C at 760 mmHg
• PKA: 13.57±0.70(Predicted)
• Flash Point: 363.863 °C
• PSA: 78.79000
• Density: 1.15 g/cm³
• LogP: 9.44200
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 7.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 654.34690077
• Heavy Atom Count: 48
• Complexity: 1040

Purity/Quality:

≥98.0% ^*data from raw suppliers

AtorvastatinAcetonidetert-ButylEster ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

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=CC=C5
• 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=CC=C5
• Uses: Atorvastatin intermediate Atorvastatin Acetonide tert-Butyl Ester (Atorvastatin EP Impurity I) is an Atorvastatin intermediate.

Technology Process of Atorvastatin Acetonide tert-Butyl Ester

There total 45 articles about Atorvastatin Acetonide tert-Butyl 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: 97.0%

C40H45FN2O5 → tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate (125971-95-1)

Guidance literature:

With palladium 10% on activated carbon; hydrogen;

DOI:10.1016/j.cclet.2011.04.016

Reference yield: 96.5%

tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (125971-86-0,125995-13-3) + 2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide (125971-96-2,125971-58-6) → tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate (125971-95-1)

Guidance literature:

With Trimethylacetic acid; In toluene; at 105 - 110 ℃; for 1h; Industrial scale;

Reference yield: 79.0%

C26H22FNO3 (1331869-19-2) + tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate (125971-86-0,125995-13-3) → tert-butyl (4R,6R)-6-{2-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)pyrrol-1-yl]ethyl}-2,2-dimethyl-1,3-dioxane-4-acetate (125971-95-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; Trimethylacetic acid; In cyclohexane; at 80 - 84 ℃; for 25h; Concentration; Reagent/catalyst; Dean-Stark; Reflux;

upstream raw materials:

tert-butyl [(4R,6R)-6-aminoethyl-2,2-dimethyl-1,3-dioxan-4-yl]acetate

2-[2-(4-fluorophenyl)-2-oxo-1-phenylethyl]-4-methyl-3-oxopentanoic acid phenylamide

4-methyl-3-oxo-N-phenylpentanamide

benzaldehyde

Downstream raw materials:

atorvastatin

[R-(R*,R*)]-2-(4-fluorophenyl)-β,δ-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic acid; ammonium salt

atorvastatin potassium

lipitor

Refernces

• 1、 Antunes, Inês F.,Clemente, Gon?alo S.,D?mling, Alexander,Elsinga, Philip H.,Rickmeier, Jens,Ritter, Tobias,Zarganes-Tzitzikas, Tryfon. "[18F]Atorvastatin: synthesis of a potential molecular imaging tool for the assessment of statin-related mechanisms of action". . . Retrieved 2020/04/24.
• 2、 -. "Separating method for impurity A and impurity B and method for effectively reducing content of impurity A in atorvastatin calcium condensate". Paragraph 0071; 0072; 0073. . Retrieved 2019/01/16.