Atorvastatin Acetonide

Base Information

• Chemical Name: Atorvastatin Acetonide
• CAS No.: 581772-29-4
• Molecular Formula: C36H39FN2O5
• Molecular Weight: 598.714
• UNII: 4P52UK6TGT
• DSSTox Substance ID: DTXSID70450295
• Nikkaji Number: J2.900.969D
• Wikidata: Q82269944
• Mol file: 581772-29-4.mol

Synonyms:Atorvastatin Acetonide;581772-29-4;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)acetic acid;4P52UK6TGT;UNII-4P52UK6TGT;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]acetic acid;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-, (4R,6R)-;Atorvastatin Impurity 2;Lipitor acetonide;SCHEMBL915229;DTXSID70450295;YFMKJVDVNPLQFO-FQLXRVMXSA-N;HY-135379;CS-0112185;ATORVASTATIN CALCIUM IMPURITY P [EP IMPURITY];[(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]acetic acid;N,4-Diphenyl-1-[2-[(4R)-2,2-dimethyl-6alpha-(2-oxo-2-hydroxyethyl)-1,3-dioxane-4alpha-yl]ethyl]-2-isopropyl-5-(4-fluorophenyl)-1H-pyrrole-3-carboxamide

Chemical Property of Atorvastatin Acetonide

Chemical Property:

• Melting Point: 73-75°C
• Boiling Point: 689.3±55.0 °C(Predicted)
• PKA: 4.24±0.10(Predicted)
• PSA: 93.28000
• Density: 1.21±0.1 g/cm3(Predicted)
• LogP: 8.49590
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 6.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 598.28430051
• Heavy Atom Count: 44
• Complexity: 941

Purity/Quality:

NLT 98% ^*data from raw suppliers

AtorvastatinAcetonide ^*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)O)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)O)C3=CC=C(C=C3)F)C4=CC=CC=C4)C(=O)NC5=CC=CC=C5
• Uses: Protected Atorvastatin.

Technology Process of Atorvastatin Acetonide

There total 26 articles about Atorvastatin Acetonide 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: 99.0%

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) → 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)acetic acid (581772-29-4)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; at 20 ℃; for 18h;

DOI:10.1016/j.bmcl.2015.12.069

Reference yield: 85.0%

5-(4-fluorophenyl)-1-{2-[(4R,6S)-6-(2-hydroxyethyl)-2,2-dimethyl-1,3-dioxan-4-yl]ethyl}-2-isopropyl-N,4-diphenyl-1H-pyrrole-3-carboxamide (697266-08-3) → 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)acetic acid (581772-29-4)

Guidance literature:

With sodium hypochlorite; sodium chlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; In aq. phosphate buffer; toluene; at 20 ℃; for 14.5h; pH=4 - 5;

DOI:10.1002/ejoc.201700387

Reference yield: 46.0%

2,2-dimethoxy-propane (77-76-9) + atorvastatin (134523-00-5,110862-48-1) → 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)acetic acid (581772-29-4)

Guidance literature:

With toluene-4-sulfonic acid; In acetone; at 20 ℃; for 15h;

upstream raw materials:

lipitor

2,2-dimethoxy-propane

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

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:

(Z)-4-hydroxybut-2-enyl 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

(3R,5R)-((Z)-4-((1-(nitrooxy)ethoxy)carbonyloxy)but-2-enyl) 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate

3,3-dimethyl-5,6-bis (nitrooxy)hexyl 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

(3R,5R)-3,3-dimethyl-5,6-bis(nitrooxy)hexyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate

Refernces

• 1、 Poh, Jian-Siang,Makai, Szabolcs,von Keutz, Timo,Tran, Duc N.,Battilocchio, Claudio,Pasau, Patrick,Ley, Steven V.. "Rapid Asymmetric Synthesis of Disubstituted Allenes by Coupling of Flow-Generated Diazo Compounds and Propargylated Amines". supporting information. p. 1864 - 1868. Retrieved 2017/02/05.
• 2、 Mizoi, Kenta,Takahashi, Masato,Haba, Masami,Hosokawa, Masakiyo. "Synthesis and evaluation of atorvastatin esters as prodrugs metabolically activated by human carboxylesterases". supporting information. p. 921 - 923. Retrieved 2016/05/24.