Icomethasone 21-Acetate

Base Information

• Chemical Name: Icomethasone 21-Acetate
• CAS No.: 24916-91-4
• Molecular Formula: C₂₄H₃₁ClO₆
• Molecular Weight: 450.96
• UNII: QMP3UNH3SX
• Mol file: 24916-91-4.mol

Synonyms:Icomethasone 21-Acetate;24916-91-4;Icometasone-21-acetate;QMP3UNH3SX;[2-[(8S,9R,10S,11S,13S,14S,16R,17R)-9-Chloro-11,17-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;UNII-QMP3UNH3SX;Mometasone furoate impurity O [EP];MOMETASONE FUROATE IMPURITY O [EP IMPURITY];9-Chloro-11beta,17-dihydroxy-16alpha-methyl-3,20-dioxopregna-1,4-dien-21-yl acetate;(11.BETA.,16.ALPHA.)-21-(ACETYLOXY)-9-CHLORO-11,17-DIHYDROXY-16-METHYLPREGNA-1,4-DIENE-3,20-DIONE;(11beta,16alpha)-21-(Acetyloxy)-9-chloro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione;9-CHLORO-11.BETA.,17-DIHYDROXY-16.ALPHA.-METHYL-3,20-DIOXOPREGNA-1,4-DIEN-21-YL ACETATE;9-Chloro-11beta,17-dihydroxy-16alpha-methyl-3,20-dioxopregna-1,4-dien-21-yl Acetate (Icometasone 21-Acetate);PREGNA-1,4-DIENE-3,20-DIONE, 21-(ACETYLOXY)-9-CHLORO-11,17-DIHYDROXY-16-METHYL-, (11.BETA.,16.ALPHA.)-;Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-9-chloro-11,17-dihydroxy-16-methyl-, (11?,16?)- (9CI);Pregna-1,4-diene-3,20-dione, 9-chloro-11?,17,21-trihydroxy-16?-methyl-, 21-acetate (7CI,8CI);Icometasone 21-Acetate;Mometasone Furoate Imp. O (EP);Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-9-chloro-11,17-dihydroxy-16-methyl-, (11beta,16alpha)-;PREGNA-1,4-DIENE-3,20-DIONE, 9-CHLORO-11.BETA.,17,21-TRIHYDROXY-16.ALPHA.-METHYL-, 21-ACETATE;Pregna-1,4-diene-3,20-dione, 9-chloro-11beta,17,21-trihydroxy-16alpha-methyl-, 21-acetate

Chemical Property of Icomethasone 21-Acetate

Chemical Property:

• Melting Point: >210°C (dec.)
• Boiling Point: 609.6±55.0 °C(Predicted)
• PKA: 12.12±0.70(Predicted)
• Density: 1.32±0.1 g/cm3(Predicted)
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly, Sonicated)
• XLogP3: 3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 450.1809164
• Heavy Atom Count: 31
• Complexity: 910

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

Icomethasone21-Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)COC(=O)C)O)C)O)Cl)C
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)COC(=O)C)O)C)O)Cl)C
• Uses: Icomethasone 21-Acetate is a 6-hydroxycorticosteroids Icomethasone (I164100) derivative.

Technology Process of Icomethasone 21-Acetate

There total 4 articles about Icomethasone 21-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: 62.0%

17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate (10106-41-9) → Acetic acid 2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-11,17-dihydroxy-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)-2-oxo-ethyl ester (24916-91-4)

Guidance literature:

With perchloric acid; 1,3-dichloro-5,5-dimethylhydantoin; In tetrahydrofuran; water; at 0 - 20 ℃;

DOI:10.1016/j.steroids.2019.04.008

Reference yield:

17α,21-dihydroxy-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate (2884-51-7) → Acetic acid 2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-11,17-dihydroxy-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)-2-oxo-ethyl ester (24916-91-4)

Guidance literature:

With hydrogenchloride; In chloroform;

Reference yield:

C27H38O4Si → Acetic acid 2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-11,17-dihydroxy-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)-2-oxo-ethyl ester (24916-91-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / -5 - 0 °C

2: hydrogenchloride / water / 3 h / 20 °C

3: perchloric acid; 1,3-dichloro-5,5-dimethylhydantoin / water; tetrahydrofuran / 0 - 20 °C

With hydrogenchloride; perchloric acid; 1,3-dichloro-5,5-dimethylhydantoin; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/j.steroids.2019.04.008

upstream raw materials:

17α,21-dihydroxy-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate

17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate

Refernces