Fluticasone Propionate Intermediate

Base Information

• Chemical Name: Fluticasone Propionate Intermediate
• CAS No.: 80474-45-9
• Molecular Formula: C24H30F2O5S
• Molecular Weight: 468.562
• European Community (EC) Number: 617-084-5
• UNII: YXC5X4NLK5
• DSSTox Substance ID: DTXSID401019402
• Mol file: 80474-45-9.mol

Synonyms:80474-45-9;Fluticasone Propionate Intermediate;YXC5X4NLK5;UNII-YXC5X4NLK5;(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioic S-acid;6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propanoyloxy-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carbothioic S-acid;6alpha,9alpha-Difluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17alpha-(propionyloxy)-androsta-1,4-diene-17beta-carbothioic Acid;(6alpha,11beta,16alpha,17alpha)-6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)androsta-1,4-diene-17-carbothioic acid;Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-, (6alpha,11beta,16alpha,17alpha)-;(6a,11b,16a,17a)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-androsta-1,4-diene-17-carbothioic acid;SCHEMBL192154;DTXSID401019402;AMY38237;AKOS015967425;(6alpha,11beta,,16alpha,17alpha)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxo-propoxy)androsta-1,4-diene-17-carbothioic acid;6|A,9|A-Difluoro-11|A-hydroxy-16|A-methyl-3-oxo-17|A-(propionyloxy)-androsta-1,4-diene-17|A-carbothioic Acid;E80375;(6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-6,9-DIFLUORO-11-HYDROXY-16-METHYL-3-OXO-17-(1-OXOPROPOXY)ANDROSTA-1,4-DIENE-17-CARBOTHIOIC ACID;(6alpha,11beta,16alpha,17alpha)-6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-androsta-1,4-diene-17-carbothioic acid;(6alpha,11beta,16alpha,17alpha)-6,9-Difluoro-11-hydroxy-16-methyl-3-oxo-17-(propionyloxy)androsta-1,4-diene-17-carbothioic S-acid;6 alpha ,9 alpha -Difluoro-11 beta -hydroxy-16 alpha -methyl-3-oxo-17 alpha -(propionyloxy)-androsta-1,4-diene-17 beta -carbothioic Acid;6?,9?-Difluoro-11?-hydroxy-16?-methyl-3-oxo-17?-(propionyloxy)-androsta-1,4-diene-17?-carbothioic Acid;6alpha,9-Difluoro-11beta-hydroxy-16alpha-methyl-3-oxo-17-(propanoyloxy)androsta-1,4-diene-17beta-carbothioic Acid;ANDROSTA-1,4-DIENE-17-CARBOTHIOIC ACID, 6,9-DIFLUORO-11-HYDROXY-16-METHYL-3-OXO-17-(1-OXOPROPOXY)-, (6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-

Chemical Property of Fluticasone Propionate Intermediate

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 158-160 °C
• Refractive Index: 1.566
• Boiling Point: 563.337 °C at 760 mmHg
• PKA: 2.99±0.70(Predicted)
• Flash Point: 294.496 °C
• PSA: 119.47000
• Density: 1.315 g/cm³
• LogP: 3.69960
• Storage Temp.: -20°C Freezer
• Water Solubility.: 50mg/L at 20℃
• XLogP3: 3.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 468.17820155
• Heavy Atom Count: 32
• Complexity: 949

Purity/Quality:

99% ^*data from raw suppliers

FluticasonePropionateIntermediate 95+% ^*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)S
• 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)S
• Uses: An intermediate in the synthesis of Fluticasone Propionate.

Technology Process of Fluticasone Propionate Intermediate

There total 14 articles about Fluticasone Propionate Intermediate 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: 96.33%

17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene (105638-31-1) → 17-propionate carbothioic acid (80474-45-9)

Guidance literature:

17β-[(N,N-dimethylcarbamoyl)thio]formyl-6α,9α-difluoro-11β-hydroxy-16α-methyl-17α-propionyloxy-3-one androstone-1,4-diene; With methanol; potassium carbonate; at 20 ℃; for 5 - 7h;

With hydrogenchloride; In water; at 20 ℃; pH=1.5 - 2.0; Product distribution / selectivity;

Reference yield: 91.0%

propionyl chloride (79-03-8) + 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid (80473-92-3) → 17-propionate carbothioic acid (80474-45-9)

Guidance literature:

propionyl chloride; 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid; With triethylamine; In dichloromethane; at -5 ℃;

With diethylamine; In acetone; for 1h; regioselective reaction;

DOI:10.1080/00304940809458122

Reference yield: 32.0%

6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid (65429-42-7) → 17-propionate carbothioic acid (80474-45-9)

Guidance literature:

6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid; With 1-methyl-1H-imidazole; In ISOPROPYLAMIDE; at 50 ℃;

With sodium hydrogensulfide; In ISOPROPYLAMIDE; at 35 ℃; for 0.25h;

With hydrogenchloride; In ISOPROPYLAMIDE; water; pH=2;

upstream raw materials:

Propionic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-propionylsulfanylcarbonyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester

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

C₂₄H₂₉F₂O₅S^(1-)*K⁽¹⁺⁾

6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid

Downstream raw materials:

flixotide

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

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

6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbonylsulfenic acid

Refernces

• 1、 -. "Preparation method of fluticasone propionate". Paragraph 0037-0039. . Retrieved 2019/10/29.
• 2、 Zhou, Jiadi,Jin, Can,Su, Weike. "Improved synthesis of fluticasone propionate". . p. 928 - 933. Retrieved 2014/10/16.