Betamethasone 17-Propionate 21-Mesylate

Base Information

• Chemical Name: Betamethasone 17-Propionate 21-Mesylate
• CAS No.: 15423-80-0
• Molecular Formula: C₂₆H₃₅FO₈S
• Molecular Weight: 526.624
• UNII: GA4A80ZP11
• DSSTox Substance ID: DTXSID30514069
• Wikidata: Q82374193
• Mol file: 15423-80-0.mol

Synonyms:15423-80-0;Betamethasone 17-Propionate 21-Mesylate;GA4A80ZP11;[(8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11-hydroxy-10,13,16-trimethyl-17-(2-methylsulfonyloxyacetyl)-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate;(11beta,16beta)-9-Fluoro-11-hydroxy-16-methyl-21-[(methylsulfonyl)oxy]-17-(1-oxopropoxy)pregna-1,4-diene-3,20-dione;(11beta,16beta)-9-Fluoro-11-hydroxy-16-methyl-21-((methylsulfonyl)oxy)-17-(1-oxopropoxy)pregna-1,4-diene-3,20-dione;Pregna-1,4-diene-3,20-dione, 9-fluoro-11-hydroxy-16-methyl-21-((methylsulfonyl)oxy)-17-(1-oxopropoxy)-, (11beta,16beta)-;Pregna-1,4-diene-3,20-dione, 9-fluoro-11-hydroxy-16-methyl-21-[(methylsulfonyl)oxy]-17-(1-oxopropoxy)-, (11beta,16beta)-;UNII-GA4A80ZP11;SCHEMBL8204087;DTXSID30514069;Clobetasol propionate impurity I [EP];CLOBETASOL PROPIONATE IMPURITY I [EP IMPURITY];(11beta,16beta)-9-Fluoro-11-hydroxy-21-[(methanesulfonyl)oxy]-16-methyl-3,20-dioxopregna-1,4-dien-17-yl propanoate;9-Fluoro-11beta-hydroxy-16beta-methyl-21-((methylsulfonyl)oxy)-3,20-dioxopregna-1,4-dien-17-yl propanoate;9-fluoro-11beta-hydroxy-16beta-methyl-21-[(methanesulfonyl)oxy]-3,20-dioxopregna-1,4-dien-17-yl propanoate,

Chemical Property of Betamethasone 17-Propionate 21-Mesylate

Chemical Property:

• Melting Point: 177-179 °C(Solv: water (7732-18-5); ethanol (64-17-5))
• Boiling Point: 659.2±55.0 °C(Predicted)
• PKA: 12.87±0.70(Predicted)
• PSA: 132.42000
• Density: 1.33±0.1 g/cm3(Predicted)
• LogP: 3.92130
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Very Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 7
• Exact Mass: 526.20366741
• Heavy Atom Count: 36
• Complexity: 1150

Purity/Quality:

99% ^*data from raw suppliers

Betamethasone17-Propionate21-Mesylate ^*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(C2CCC4=CC(=O)C=CC43C)F)O)C)C)C(=O)COS(=O)(=O)C
• Isomeric SMILES: CCC(=O)O[C@@]1([C@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)O)C)C)C(=O)COS(=O)(=O)C
• Uses: Betamethasone 17-Propionate 21-Mesylate is the 21-mesylate analogue of Betamethasone 17-Acetate (B327015) with antiinflammatory activity.

Technology Process of Betamethasone 17-Propionate 21-Mesylate

There total 4 articles about Betamethasone 17-Propionate 21-Mesylate 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:

betamethasone (378-44-9) → betamethasone 17-propanoate 21-mesylate (15423-80-0)

Guidance literature:

Multi-step reaction with 2 steps

1: p-toluenesulfonic acid / dimethylformamide; benzene / 1.25 h / Ambient temperature

2: pyridine / 1.5 h / 0 - 5 °C

With toluene-4-sulfonic acid; In pyridine; N,N-dimethyl-formamide; benzene;

DOI:10.1248/cpb.37.3286

Reference yield:

Betamethasone propionate (5534-13-4) + methanesulfonyl chloride (124-63-0) → betamethasone 17-propanoate 21-mesylate (15423-80-0)

Guidance literature:

In pyridine; at 0 - 5 ℃; for 1.5h;

DOI:10.1248/cpb.37.3286

Reference yield:

→ Propionic acid (9R,10S,11S,13S,16S,17R)-9-fluoro-11-hydroxy-17-(2-methanesulfonyloxy-acetyl)-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester (15423-80-0,15423-90-2)

Guidance literature:

Betamethason-17-propionat, MeSO2Cl;

upstream raw materials:

Betamethasone propionate

methanesulfonyl chloride

betamethasone

Refernces