Dexamethasone 9,11-Epoxide

Base Information

• Chemical Name: Dexamethasone 9,11-Epoxide
• CAS No.: 24916-90-3
• Molecular Formula: C22H28O5
• Molecular Weight: 372.461
• Hs Code.: 2937290090
• European Community (EC) Number: 246-529-2
• UNII: 45O198JS6W
• DSSTox Substance ID: DTXSID10862499
• Nikkaji Number: J286.424J
• Mol file: 24916-90-3.mol

Synonyms:24916-90-3;Dexamethasone 9,11-Epoxide;16-Alpha-Methylepoxide;UNII-45O198JS6W;45O198JS6W;EINECS 246-529-2;9beta,11beta-Epoxy-17,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione;EC 246-529-2;(1S,2S,10S,11S,13R,14R,15S,17R)-14-Hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyl-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadeca-3,6-dien-5-one;(1S,2S,10S,11S,13R,14R,15S,17S)-14-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyl-18-oxapentacyclo[8.8.0.01,17.02,7.011,15]octadeca-3,6-dien-5-one;C22H28O5;16alpha-Methylepoxide;16-Alpha Methyl Epoxide;8DM;Dexamethasone Imp. D (EP);17,21-Dihydroxy-16alpha-methyl-9beta,11beta-epoxypregna-1,4-diene-3,20-dione;Dexamethasone Impurity D;Mometasone Furoate Impurity L;DOB-MN;(9b,11b,16a)-9,11-Epoxy-17,21-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione;SCHEMBL5261130;9|A,11|A-Epoxy-17,21-dihydroxy-16|A-methylpregna-1,4-diene-3,20-dione;DTXSID10862499;GBDXNHBVYAMODG-QDBZYVRYSA-N;Pregna-1,4-dieno-3,20-diona, 9,11-epoxi-17,21-dihidroxi-16-metil-, (9?,11?,16?)-;AMY14575;HY-N0348;AKOS015895224;AC-1550;CS-6951;CS-T-52335;AS-80742;DEXAMETHASONE IMPURITY D [EP IMPURITY];D97367;A817550;MOMETASONE FUROATE IMPURITY L [EP IMPURITY];Q27258856;(9B,11b,16a)-9,11-epoxy-17,21-dihydroxy-16-methylpregna-1,4-diene-3,20-dione;9 beta ,11 beta -Epoxy-17,21-dihydroxy-16 alpha -methylpregna-1,4-diene-3,20-dione;9beta,11beta-epoxy-17alpha,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione;(1S,2S,10S,11S,13R,14R,15S,17S)-14-HYDROXY-14-(2-HYDROXYACETYL)-2,13,15-TRIMETHYL-18-OXAPENTACYCLO[8.8.0.0(1),(1)?.0(2),?.0(1)(1),(1)?]OCTADECA-3,6-DIEN-5-ONE;(4aS,4bS,5aS,6aS,7R,8R,9aS,9bS)-7-Hydroxy-7-(2-hydroxyacetyl)-4a,6a,8-trimethyl-5a,6,6a,7,8,9,9a,9b,10,11-decahydrocyclopenta[1,2]phenanthro[4,4a-b]oxiren-2(4aH)-one;9.BETA.,11.BETA.-EPOXY-17,21-DIHYDROXY-16.ALPHA.-METHYLPREGNA-1,4-DIENE-3,20-DIONE;9.BETA.-PREGNA-1,4-DIENE-3,20-DIONE, 9,11.BETA.-EPOXY-17,21-DIHYDROXY-16.ALPHA.-METHYL-;PREGNA-1,4-DIENE-3,20-DIONE, 9,11-EPOXY-17,21-DIHYDROXY-16-METHYL-, (9.BETA.,11.BETA.,16.ALPHA.)-;Pregna-1,4-diene-3,20-dione, 9,11-epoxy-17,21-dihydroxy-16-methyl-, (9beta,11beta,16alpha)-

Chemical Property of Dexamethasone 9,11-Epoxide

Chemical Property:

• Appearance/Colour: pale-yellow solid
• Vapor Pressure: 4.09E-15mmHg at 25°C
• Melting Point: 210-220 °C
• Refractive Index: 1.616
• Boiling Point: 564.9 °C at 760 mmHg
• PKA: 12.56±0.70(Predicted)
• Flash Point: 198.103 °C
• PSA: 87.13000
• Density: 1.324 g/cm³
• LogP: 1.96410
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly, Heated, Sonicated), DMSO (Slightly, Sonicated), Methanol (
• XLogP3: 2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 372.19367399
• Heavy Atom Count: 27
• Complexity: 814

Purity/Quality:

99%, ^*data from raw suppliers

Dexamethasone 9,11-epoxide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C35C(O5)CC2(C1(C(=O)CO)O)C)C
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]35[C@@H](O5)C[C@@]2([C@]1(C(=O)CO)O)C)C
• Uses: A metabolite of Mometasone furoate.

Technology Process of Dexamethasone 9,11-Epoxide

There total 9 articles about Dexamethasone 9,11-Epoxide 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: 93.3%

C26H33BrO8 → 17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione (24916-90-3)

Guidance literature:

With sodium hydroxide; In methanol; dichloromethane; at 0 - 5 ℃;

DOI:10.1021/op0102013

Reference yield: 84.0%

17α,21-dihydroxy-9β,11β-epoxy-16α-methylpregna-1,4-diene-3,20-dione 21-acetate (2884-51-7) → 17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione (24916-90-3)

Guidance literature:

With sodium hydroxide; In methanol; at -10 - -5 ℃; for 2h; Reagent/catalyst; Temperature;

Reference yield:

11α,17,21-trihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione (78761-59-8) → 17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione (24916-90-3)

Guidance literature:

Multi-step reaction with 4 steps

1: triethylamine / dichloromethane / -15 °C

2: phosphorus pentachloride / tetrahydrofuran / -85 °C

3: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; N,N-dimethyl-formamide / 1 h / 20 °C

4: sodium hydroxide / dichloromethane; methanol / 0 - 5 °C

With perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; phosphorus pentachloride; triethylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/op0102013

upstream raw materials:

11α,17,21-trihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione

17α-hydroxy-16α-methyl-21-ethoxycarbonyloxypregna-1,4,9(11)-triene-3,20-dione

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

Downstream raw materials:

epoxyparamethasone

9α-chloro-11β,17α-dihydroxy-17β-(2,2-dioxido-3,4-dehydro-1,2-oxathiolan-4-yl)-16α-methylandrosta-1,4-dien-3-one 17-(2-furoate)

9,11-Epoxidemometasone furoate

Mometasone furoate

Refernces

• 1、 Das, Saibal Kumar,Dubey, Manoj Kumar,Buchhikonda, Ravinder. "Improvements in corticosteroid 21-acetoxy-17α-hydroxy-16α-methyl-pregna-1,4,9(11)-triene-3,20-dione synthesis and its use as common intermediate in the synthesis of some impurities related to dexamethasone and mometasone". . p. 47 - 55. Retrieved 2019/05/22.
• 2、 -. "16α-methylation process". . . Retrieved 2008/06/13.