(3S,5S)-Atorvastatin Sodium Salt

Base Information

• Chemical Name: (3S,5S)-Atorvastatin Sodium Salt
• CAS No.: 134523-01-6
• Molecular Formula: C33H35FN2O5^.Na
• Molecular Weight: 580.632
• European Community (EC) Number: 828-055-3
• DSSTox Substance ID: DTXSID60928655
• Mol file: 134523-01-6.mol

Synonyms:(3S,5S)-Atorvastatin Sodium Salt;(3S,5S)-Atorvastatin (sodium salt);1428118-38-0;sodium;(3S,5S)-7-[2-(4-fluorophenyl)-3-phenyl-4-(phenylcarbamoyl)-5-propan-2-ylpyrrol-1-yl]-3,5-dihydroxyheptanoate;3S,5S-Atorvastatin Sodium;DTXSID60928655;AKOS025394708;(betaS,deltaS)-2-(4-Fluorophenyl)-beta,delta-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrole-1-heptanoic Acid Sodium;Sodium 7-[2-(4-fluorophenyl)-4-[hydroxy(phenylimino)methyl]-3-phenyl-5-(propan-2-yl)-1H-pyrrol-1-yl]-3,5-dihydroxyheptanoate

Chemical Property of (3S,5S)-Atorvastatin Sodium Salt

Chemical Property:

• Boiling Point: 722.2±60.0 °C at 760 mmHg
• PKA: 4.46(at 25℃)
• Flash Point: 390.6±32.9 °C
• PSA: 114.62000
• Density: 1.2±0.1 g/cm³
• LogP: 5.05190
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Methanol (Slightly), Water (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 580.23494463
• Heavy Atom Count: 42
• Complexity: 829

Purity/Quality:

98%,99%, ^*data from raw suppliers

(3R,5R)-AtorvastatinSodiumSalt ^*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)[O-])O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4.[Na+]
• Isomeric SMILES: CC(C)C1=C(C(=C(N1CC[C@@H](C[C@@H](CC(=O)[O-])O)O)C2=CC=C(C=C2)F)C3=CC=CC=C3)C(=O)NC4=CC=CC=C4.[Na+]
• Uses: (3R,5R)-Atorvastatin Sodium Salt is an Atorvastatin impurity in bulk drug and tablets.

Technology Process of (3S,5S)-Atorvastatin Sodium Salt

There total 26 articles about (3S,5S)-Atorvastatin Sodium Salt 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: 97.7%

(3R,5R)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4-phenylcarbamoylpyrrol-1-yl]-3,5-dihydroxyheptanoic acid t-butyl ester (134395-00-9) → atorvastatin sodium (134523-01-6)

Guidance literature:

With sodium hydroxide; water; In 1,4-dioxane; tert-butyl methyl ether; for 21h; Product distribution / selectivity; Heating / reflux;

Reference yield:

lipitor (134523-03-8) → atorvastatin sodium (134523-01-6)

Guidance literature:

lipitor; With hydrogenchloride; In tetrahydrofuran; water; at 20 ℃;

With sodium hydroxide; In methanol; water; Heating / reflux;

Reference yield:

4-fluorobenzaldehyde (459-57-4) → atorvastatin sodium (134523-01-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 2) NEt₃ / 1) ethyl thiazolium catalyst / or with methyl thiazolium catalyst; 1) EtOH

2: 75 percent / pivalic acid / toluene; heptane; tetrahydrofuran / Heating

3: aq. HCl / methanol

4: aq. NaOH / methanol

With hydrogenchloride; sodium hydroxide; triethylamine; Trimethylacetic acid; ethyl thiazolium catalyst; In tetrahydrofuran; methanol; n-heptane; toluene;

DOI:10.1016/S0040-4039(00)74190-6

upstream raw materials:

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

lipitor

4-fluorobenzaldehyde

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

Downstream raw materials:

lipitor

atorvastatin

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

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

Refernces

• 1、 -. "PROCESS FOR THE CONTINUOUS MANUFACTURE OF STATINS". Page/Page column 27-30. . Retrieved 2021/06/04.
• 2、 -. "Preparation method of crystal form I atorvastatin calcium". Paragraph 0043-0044; 0052-0053; 0058-0059; 0064-0065. . Retrieved 2020/02/29.