Fluticasone propionate-17beta-carboxylic acid

Base Information

• Chemical Name: Fluticasone propionate-17beta-carboxylic acid
• CAS No.: 65429-42-7
• Molecular Formula: C24H30F2O6
• Molecular Weight: 452.495
• European Community (EC) Number: 813-979-1
• UNII: TP537C010A
• DSSTox Substance ID: DTXSID70215760
• Nikkaji Number: J3.298.616A
• Wikidata: Q27290090
• ChEMBL ID: CHEMBL3542318
• Mol file: 65429-42-7.mol

Synonyms:fluticasone propionate-17-carboxylic acid;fluticasone propionate-17beta-carboxylic acid;FP17betaCA

Chemical Property of Fluticasone propionate-17beta-carboxylic acid

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 219-220 °C
• Refractive Index: 1.561
• Boiling Point: 577.645 °C at 760 mmHg
• PKA: 2.51±0.70(Predicted)
• Flash Point: 303.149 °C
• PSA: 100.90000
• Density: 1.333 g/cm³
• LogP: 3.32780
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Methanol (Slightly, Heated, Sonicated)
• XLogP3: 2.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 452.20104500
• Heavy Atom Count: 32
• Complexity: 945

Purity/Quality:

99% ^*data from raw suppliers

Fluticasone17β-CarboxylicAcidPropionate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)OC1(C(CC2C1(CC(C3(C2CC(C4=CC(=O)C=CC43C)F)F)O)C)C)C(=O)O
• Isomeric SMILES: CCC(=O)O[C@@]1([C@@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2C[C@@H](C4=CC(=O)C=C[C@@]43C)F)F)O)C)C)C(=O)O
• Uses: An impurity formed in the synthesis of Fluticasone propionate (F599500).

Technology Process of Fluticasone propionate-17beta-carboxylic acid

There total 9 articles about Fluticasone propionate-17beta-carboxylic acid 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%

propionyl chloride (79-03-8) + 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid (28416-82-2) → 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid (65429-42-7)

Guidance literature:

propionyl chloride; 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid; With diethylamine; triethylamine; In acetone; at 0 ℃; for 2.33333h;

With hydrogenchloride; In water; pH=2;

Reference yield: 98.6%

propionic acid anhydride (123-62-6) + 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid (28416-82-2) → 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid (65429-42-7)

Guidance literature:

propionic acid anhydride; 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid; With triethylamine; In acetone; at 10 - 30 ℃; for 4h;

With diethylamine; In acetone; at 10 - 20 ℃; for 1h;

Reference yield:

propionyl chloride (79-03-8) + diethylamine (109-89-7) + pentan-3-one (96-22-0) + 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid (28416-82-2) + butanone (78-93-3) → 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid (65429-42-7)

Guidance literature:

With hydrogenchloride; triethylamine; In water; acetone;

upstream raw materials:

propionyl chloride

6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid

11β,17α,21-trihydroxy-6α,9α-difluoro-16β-methylpregna-1,4-diene-3,20-dione

6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid

Downstream raw materials:

17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene

6α,9α-difluoro-11β-hydroxy-17β-<(methylthio)carbonyl>-17α-(propionyloxy)-16α-methylandrosta-1,4-dien-3-one

S-iodomethyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-oxo-androsta-1,4-diene-17β-carbothioate

S-chloromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate

Refernces

• 1、 -. "METHODS OF PREPARING INTERMEDIATE OF FLUTICASONE PROPIONATE". Paragraph 0044; 0050; 0051. . Retrieved 2016/04/26.
• 2、 Zhou, Jiadi,Jin, Can,Su, Weike. "Improved synthesis of fluticasone propionate". . p. 928 - 933. Retrieved 2014/10/16.