Fluticasone acetate

Base Information

• Chemical Name: Fluticasone acetate
• CAS No.: 80474-24-4
• Molecular Formula: C₂₄H₂₉F₃O₅S
• Molecular Weight: 486.552
• European Community (EC) Number: 831-667-3
• UNII: 1BIA3ZKX8V
• DSSTox Substance ID: DTXSID10230351
• Nikkaji Number: J624.658C
• Wikidata: Q27252198
• Mol file: 80474-24-4.mol

Synonyms:Fluticasone acetate;80474-24-4;UNII-1BIA3ZKX8V;1BIA3ZKX8V;[(6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-(fluoromethylsulfanylcarbonyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] acetate;17-yl ester;SCHEMBL11223816;DTXSID10230351;FLUTICASONE PROPIONATE IMPURITY C [EP IMPURITY];Q27252198;11beta-Hydroxy-6alpha,9-difluoro-16alpha-methyl-3-oxo-17-acetoxyandrosta-1,4-diene-17beta-thiocarboxylic acid S-(fluoromethyl) ester;6.ALPHA.,9-DIFLUORO-17-(((FLUOROMETHYL)SULFANYL)CARBONYL)-11.BETA.-HYDROXY-16.ALPHA.-METHYL-3-OXOANDROSTA-1,4-DIEN-17.ALPHA.-YL ACETATE;Acetic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-17-fluoromethylsulfanylcarbonyl-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-;ANDROSTA-1,4-DIENE-17-CARBOTHIOIC ACID, 17-(ACETYLOXY)-6,9-DIFLUORO-11-HYDROXY-16-METHYL-3-OXO-, S-(FLUOROMETHYL) ESTER, (6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-;S-FLUOROMETHYL 17.ALPHA.-ACETYLOXY-6.ALPHA.,9.ALPHA.-DIFLUORO-11.BETA.-HYDROXY-16.ALPHA.-METHYL-3-OXO-ANDROSTA-1,4-DIENE-17.BETA.-CARBOTHIOATE

Chemical Property of Fluticasone acetate

Chemical Property:

• Boiling Point: 557.9±50.0 °C(Predicted)
• PKA: 12.61±0.70(Predicted)
• PSA: 105.97000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 4.03990
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 5
• Exact Mass: 486.16877968
• Heavy Atom Count: 33
• Complexity: 968

Purity/Quality:

95%, ^*data from raw suppliers

FluticasoneAcetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)SCF)OC(=O)C)C)O)F)C)F
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)SCF)OC(=O)C)C)O)F)C)F
• Uses: Fluticasone Acetate is an impurity of Fluticasone Propionate (F599500), a derivative of Flumethasone (F455000). An antiallergic; anti-asthmatic; anti-inflammatory.

Technology Process of Fluticasone acetate

There total 8 articles about Fluticasone acetate 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: 70.0%

S-iodomethyl 17α-acetoxy-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate (80474-71-1) → S-fluoromethyl 17α-acetoxy-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate (80474-24-4)

Guidance literature:

With silver fluoride; In acetonitrile; Ambient temperature;

DOI:10.1021/jm00048a008

Reference yield:

6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid (80473-92-3) → S-fluoromethyl 17α-acetoxy-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate (80474-24-4)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / CH₂Cl₂ / 0.75 h

2: Et₂NH / acetone / 1 h

3: 74 percent / NaHCO₃ / N,N-dimethyl-acetamide / 2 h

4: 82 percent / NaI / acetone / Heating

5: 70 percent / AgF / acetonitrile / Ambient temperature

With silver fluoride; sodium hydrogencarbonate; diethylamine; triethylamine; sodium iodide; In dichloromethane; N,N-dimethyl acetamide; acetone; acetonitrile;

DOI:10.1021/jm00048a008

Reference yield:

6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid (28416-82-2) → S-fluoromethyl 17α-acetoxy-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate (80474-24-4)

Guidance literature:

Multi-step reaction with 7 steps

1: dimethylformamide / 4 h / Ambient temperature

2: H₂S / dimethylformamide

3: Et₃N / CH₂Cl₂ / 0.75 h

4: Et₂NH / acetone / 1 h

5: 74 percent / NaHCO₃ / N,N-dimethyl-acetamide / 2 h

6: 82 percent / NaI / acetone / Heating

7: 70 percent / AgF / acetonitrile / Ambient temperature

With hydrogen sulfide; silver fluoride; sodium hydrogencarbonate; diethylamine; triethylamine; sodium iodide; In dichloromethane; N,N-dimethyl acetamide; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jm00048a008

upstream raw materials:

S-iodomethyl 17α-acetoxy-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carbothioate

6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid

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

17α-acetyloxy-6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-androsta-1,4-diene-17β-carbothioic acid

Refernces

• 1、 -. "ANDROSTANE CARBOTHIOATES". . . Retrieved 2008/06/13.