Cloticasone propionate

Base Information

• Chemical Name: Cloticasone propionate
• CAS No.: 80486-69-7
• Molecular Formula: C25H31ClF2O5S
• Molecular Weight: 517.034
• UNII: 633N8637G3
• Nikkaji Number: J624.657E
• Wikidata: Q27263558
• NCI Thesaurus Code: C80541
• ChEMBL ID: CHEMBL2106066
• Mol file: 80486-69-7.mol

Synonyms:CLOTICASONE PROPIONATE;80486-69-7;CCI 18773;Cloticasone propionate [USAN];UNII-633N8637G3;CCI-18773;[(6S,8S,9R,10S,11S,13S,14S,16R,17R)-17-(chloromethylsulfanylcarbonyl)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate;633N8637G3;Cloticasone propionate (USAN);S-(Chloromethyl) 6alpha,9-difluoro-11beta,17-dihydroxy-16alpha-methyl-3-oxoandrosta-1,4-diene-17beta-carbothioate, 17-propionate;S-Chlorofluticasone propionate;SCHEMBL42706;CHEMBL2106066;D03569;Q27263558;11beta-Hydroxy-6alpha,9-difluoro-16alpha-methyl-3-oxo-17-(propionyloxy)androsta-1,4-diene-17beta-thiocarboxylic acid S-(chloromethyl) ester;ANDROSTA-1,4-DIENE-17-CARBOTHIOIC ACID, 6,9-DIFLUORO-11-HYDROXY-16-METHYL-3-OXO-17-(1-OXOPROPOXY)-, S-(CHLOROMETHYL) ESTER, (6.ALPHA.,11.BETA.,16.ALPHA.,17.ALPHA.)-;Androsta-1,4-diene-17-carbothioic acid, 6,9-difluoro-11-hydroxy-16-methyl-3-oxo-17-(1-oxopropoxy)-, S-(chloromethyl) ester, (6alpha,11beta,16alpha,17alpha)-

Chemical Property of Cloticasone propionate

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 583.9°Cat760mmHg
• PKA: 12.53±0.70(Predicted)
• Flash Point: 307°C
• PSA: 105.97000
• Density: 1.34g/cm³
• LogP: 4.69930
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 516.1548793
• Heavy Atom Count: 34
• Complexity: 986

Purity/Quality:

95%, ^*data from raw suppliers

CloticasonePropionate ^*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)SCCl
• 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)SCCl

Technology Process of Cloticasone propionate

There total 9 articles about Cloticasone propionate 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: 67.0%

chlorobromomethane (74-97-5) + 17-propionate carbothioic acid (80474-45-9) → S-chloromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate (80486-69-7)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl acetamide; for 2h;

DOI:10.1021/jm00048a008

Reference yield:

chlorobromomethane (74-97-5) + propanethioic acid (1892-31-5,5512-76-5) + 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid (28416-82-2) → S-chloromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate (80486-69-7)

Guidance literature:

6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-3-oxoandrosta-1,4-diene-17β-carboxylic acid; With 1,1'-carbonyldiimidazole; In acetonitrile; at 5 ℃; for 18h; Inert atmosphere;

propanethioic acid; In acetonitrile; for 7h; Inert atmosphere;

chlorobromomethane;

Reference yield:

6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-(propionyloxy)androsta-1,4-diene-17β-carboxylic acid (65429-42-7) → S-chloromethyl 6α,9α-difluoro-11β-hydroxy-16α-methyl-3-oxo-17α-propionyloxyandrosta-1,4-diene-17β-carbothioate (80486-69-7)

Guidance literature:

Multi-step reaction with 3 steps

1: Et₃N / CH₂Cl₂ / 20 °C

2: Et₂NH / Heating

3: 67 percent / NaHCO₃ / N,N-dimethyl-acetamide / 2 h

With sodium hydrogencarbonate; diethylamine; triethylamine; In dichloromethane; N,N-dimethyl acetamide;

DOI:10.1021/jm00048a008

upstream raw materials:

chlorobromomethane

17-propionate carbothioic acid

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

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

Downstream raw materials:

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

flixotide

Propionic acid (6S,8S,9R,10S,11S,13S,14S,16R,17R)-6,9-difluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(toluene-4-sulfonyloxymethylsulfanylcarbonyl)-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester

Refernces

• 1、 Phillipps,Bailey,Bain,Borella,Buckton,Clark,Doherty,English,Fazakerley,Laing,Lane-Allman,Robinson,Sandford,Sharratt,Steeples,Stonehouse,Williamson. "Synthesis and structure-activity relationships in a series of antiinflammatory corticosteroid analogues, halomethyl androstane-17β- carbothioates and -17β-carboselenoates". . p. 3717 - 3729. Retrieved 2007/10/02.