9-Fluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-methanesulphonate

Base Information

• Chemical Name: 9-Fluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-methanesulphonate
• CAS No.: 382-66-1
• Molecular Formula: C22H29 F O7 S
• Molecular Weight: 456.532
• European Community (EC) Number: 206-844-8
• DSSTox Substance ID: DTXSID50959150
• Mol file: 382-66-1.mol

Synonyms:EINECS 206-844-8;382-66-1;9-Fluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-methanesulphonate;Pregna-1,4-diene-3,20-dione, 9-fluoro-11beta,17,21-trihydroxy-, 21-methanesulfonate;Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17-dihydroxy-21-((methylsulfonyl)oxy)-, (11beta)-;C22H29FO7S;C22-H29-F-O7-S;DTXSID50959150;9-Fluoro-11,17-dihydroxy-3,20-dioxopregna-1,4-dien-21-yl methanesulfonate;9-Fluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-methanesulfonate

Chemical Property of 9-Fluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-methanesulphonate

Chemical Property:

• Boiling Point: 652.2°Cat760mmHg
• PKA: 11.90±0.70(Predicted)
• Flash Point: 348.2°C
• PSA: 126.35000
• Density: 1.41g/cm³
• LogP: 2.71440
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 456.16180260
• Heavy Atom Count: 31
• Complexity: 998

Purity/Quality:

99% ^*data from raw suppliers

(11β)-9-Fluoro-11,17-dihydroxy-21-[(methylsulfonyl)oxy]pregna-1,4-diene-3,20-dione ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC(C3(C(C1CCC2(C(=O)COS(=O)(=O)C)O)CCC4=CC(=O)C=CC43C)F)O
• Isomeric SMILES: C[C@]12C[C@@H](C3([C@H]([C@@H]1CC[C@@]2(C(=O)COS(=O)(=O)C)O)CCC4=CC(=O)C=C[C@@]43C)F)O
• Uses: (11β)-9-Fluoro-11,17-dihydroxy-21-[(methylsulfonyl)oxy]pregna-1,4-diene-3,20-dione is an intermediate used in the synthesis of Desmethyl Fluorometholone (D291980), which acts as a glucocorticoid, a steroid for treatment of ocular inflammation. It is an impurity of Fluorometholone (F593145) synthesis.

Technology Process of 9-Fluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-methanesulphonate

There total 9 articles about 9-Fluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 21-methanesulphonate 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:

fludrocortisone acetate (514-36-3) → 9-fluoro-11β,17-dihydroxy-21-methanesulfonyloxy-pregna-1,4-diene-3,20-dione (382-66-1)

Guidance literature:

Multi-step reaction with 4 steps

1: palladium / Hydrogenation

2: bromine; acetic acid / Erhitzen des Reaktionsprodukts mit 2,4,6-Trimethyl-pyridin

3: aqueous methanol.K₂CO₃

With bromine; potassium carbonate; palladium; acetic acid;

DOI:10.1021/ja01620a076

Reference yield:

prednisolone 21-acetate (52-21-1) → 9-fluoro-11β,17-dihydroxy-21-methanesulfonyloxy-pregna-1,4-diene-3,20-dione (382-66-1)

Guidance literature:

Multi-step reaction with 6 steps

1: methanesulfonyl chloride; pyridine

2: aqueous HClO₄

3: potassium acetate; ethanol

4: HF

5: aqueous methanol.K₂CO₃

With pyridine; perchloric acid; ethanol; hydrogen fluoride; potassium acetate; potassium carbonate; methanesulfonyl chloride;

DOI:10.1021/ja01620a076

Reference yield:

pregna-1,4,9(11)-triene-17α,21-diol-3,20-dione 21-acetate (4380-55-6) → 9-fluoro-11β,17-dihydroxy-21-methanesulfonyloxy-pregna-1,4-diene-3,20-dione (382-66-1)

Guidance literature:

Multi-step reaction with 5 steps

1: aqueous HClO₄

2: potassium acetate; ethanol

3: HF

4: aqueous methanol.K₂CO₃

With perchloric acid; ethanol; hydrogen fluoride; potassium acetate; potassium carbonate;

DOI:10.1021/ja01620a076

upstream raw materials:

isoflupredone

methanesulfonyl chloride

fludrocortisone acetate

prednisolone 21-acetate

Downstream raw materials:

9-fluoro-11β,17-dihydroxy-pregna-1,4-diene-3,20-dione