(3R,5R)-tert-Butyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate

Base Information

• Chemical Name: (3R,5R)-tert-Butyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate
• CAS No.: 134395-00-9
• Molecular Formula: C37H43FN2O5
• Molecular Weight: 614.757
• Hs Code.: 2934999090
• European Community (EC) Number: 603-817-6
• DSSTox Substance ID: DTXSID30459683
• Nikkaji Number: J3.204.784J
• Wikidata: Q72444040
• Mol file: 134395-00-9.mol

Synonyms:134395-00-9;Atorvastatin tert-Butyl Ester;(3R,5R)-tert-Butyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate;tert-butyl (3R,5R)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoate;C37H43FN2O5;SCHEMBL538509;DTXSID30459683;GCPKKGVOCBYRML-LOYHVIPDSA-N;ATORVASTATIN TERTBUTYL ESTER;MFCD09839952;DS-15506;CS-0154132;(?R,?R)-Atorvastatin tert-Butyl Ester (>90%);A887926;J-006530;(BetaR,DeltaR)-Atorvastatin tert-Butyl Ester (>90%);(3R,5R)-7-[2-(4-Fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrole-1-yl]-3,5-dihydroxyheptanoic acid tert-butyl ester;(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid, t-butyl ester;(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoyl-pyrrol-1-yl]-3,5dihydroxy-heptanoic acid, t-butyl ester;(3R,5R)-tert-Butyl7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate;(3R5R)-tert-Butyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-35-dihydroxyheptanoate;2-(4-Fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic Acid 1,1-Dimethylethyl Ester

Chemical Property of (3R,5R)-tert-Butyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate

Chemical Property:

• Melting Point: 66-68ºC
• Boiling Point: 721.0±60.0 °C(Predicted)
• PKA: 13.57±0.70(Predicted)
• PSA: 100.79000
• Density: 1.16
• LogP: 7.64370
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slig
• XLogP3: 6.3
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 14
• Exact Mass: 614.31560064
• Heavy Atom Count: 45
• Complexity: 920

Purity/Quality:

≥98.0% ^*data from raw suppliers

(βR,δR)-Atorvastatintert-ButylEster(>90%) ^*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)OC(C)(C)C)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4
• Isomeric SMILES: CC(C)C1=C(C(=C(N1CC[C@H](C[C@H](CC(=O)OC(C)(C)C)O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4
• Uses: An impurity arising in the synthesis of Atorvastatin

Technology Process of (3R,5R)-tert-Butyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate

There total 41 articles about (3R,5R)-tert-Butyl 7-(2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-(phenylcarbamoyl)-1H-pyrrol-1-yl)-3,5-dihydroxyheptanoate 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%

→ (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester (134395-00-9)

Guidance literature:

In isopropyl alcohol; Purification / work up;

Reference yield: 98.9%

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) → (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester (134395-00-9)

Guidance literature:

With hydrogenchloride; water; In acetonitrile; for 13h; Product distribution / selectivity;

Reference yield:

4-methyl-3-oxo-N-phenylpentanamide (124401-38-3) → (3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester (134395-00-9)

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: HCl / tetrahydrofuran; H₂O / 20 °C

With hydrogenchloride; 3-ethyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazolium bromide; acetic acid; triethylamine; 3-amino propanoic acid; Trimethylacetic acid; In tetrahydrofuran; ethanol; hexane; n-heptane; water; toluene; 1: Condensation / 2: Addition / 3: Cycloaddition / 4: Hydrolysis;

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

upstream raw materials:

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

4-methyl-3-oxo-N-phenylpentanamide

benzaldehyde

4-methyl-3-oxo-N-phenyl-2-(phenylmethylene)pentanamide

Downstream raw materials:

atorvastatin sodium

atorvastatin

lipitor

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

Refernces

• 1、 -. "Method for purifying atorvastatin calcium intermediate". Paragraph 0043; 0046; 0049; 0052; 0055; 0058; 0062. . Retrieved 2021/09/01.
• 2、 -. "AN IMPROVED AND COMMERCIALLY VIABLE PROCESS FOR PREPARATION OF PYRROLE DERIVATIVES WITH IMPROVED IMPURITY PROFILE & MINIMISATION OF UNIT OPERATIONS.". Page/Page column 70; 72; 73; 74. . Retrieved 2020/02/14.