11beta,21-Dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate

Base Information

• Chemical Name: 11beta,21-Dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate
• CAS No.: 3044-42-6
• Molecular Formula: C23H28 O5
• Molecular Weight: 384.472
• European Community (EC) Number: 221-250-9
• DSSTox Substance ID: DTXSID20952779
• Nikkaji Number: J205.352G
• Wikidata: Q76009835
• Mol file: 3044-42-6.mol

Synonyms:3044-42-6;(11b)-21-(Acetyloxy)-11-hydroxypregna-1,4,16-triene-3,20-dione;11beta,21-Dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate;EINECS 221-250-9;[2-[(8S,9S,10R,11S,13S,14S)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;C23H28O5;21-acetoxy-11bhydroxypregna-1,4,16-triene-3,20-dione;SCHEMBL9488523;DTXSID20952779;AKOS027326625;BS-49822;E73722;11-Hydroxy-3,20-dioxopregna-1,4,16-trien-21-yl acetate;21-acetoxy-11beta-hydroxy-1,4,16-pregnatriene-3,20-dione;21-acetoxy-11beta-hydroxyl-1,4,16-pregnatriene-3,20-dione;21-Acetyloxy-11beta-hydroxypregna-1,4,16-triene-3,20-dione;(11?)-11-Hydroxy-3,20-dioxopregna-1,4,16-trien-21-yl acetate;(11BETA)-21-(ACETYLOXY)-11-HYDROXYPREGNA-1,4,16-TRIENE-3,20-DIONE;Pregna-1,4,16-triene-3,20-dione, 21-(acetyloxy)-11-hydroxy-, (11.beta.)-;Pregna-1,4,16-triene-3,20-dione, 21-(acetyloxy)-11-hydroxy-, (11beta)-;2-[(1S)-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6,13-trien-14-y

Chemical Property of 11beta,21-Dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate

Chemical Property:

• Vapor Pressure: 1.5E-14mmHg at 25°C
• Melting Point: 208-209 °C
• Boiling Point: 553.4°Cat760mmHg
• PKA: 14.30±0.70(Predicted)
• Flash Point: 189.9°C
• PSA: 80.67000
• Density: 1.24g/cm³
• LogP: 2.93360
• Solubility.: DCM, Ethyl Acetate
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 384.19367399
• Heavy Atom Count: 28
• Complexity: 834

Purity/Quality:

99.9% ^*data from raw suppliers

(11b)-21-(Acetyloxy)-11-hydroxypregna-1,4,16-triene-3,20-dione 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC(=O)C1=CCC2C1(CC(C3C2CCC4=CC(=O)C=CC34C)O)C
• Isomeric SMILES: CC(=O)OCC(=O)C1=CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)C=C[C@]34C)O)C
• Uses: 21-Acetoxy-11β-hydroxypregna-1,4,16-triene-3,20-dione is an intermediate in the synthesis of Budesonide (B689490) related derivatives.

Technology Process of 11beta,21-Dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate

There total 17 articles about 11beta,21-Dihydroxypregna-1,4,16-triene-3,20-dione 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: 93.0%

9-bromotriene acetate → 21-acetoxy-11β-hydroxyl-1,4,16-pregnatriene-3,20-dione (3044-42-6)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In tetrahydrofuran; for 0.5h; Inert atmosphere; Reflux;

DOI:10.1039/c9ra03673c

Reference yield: 89.8%

prednisolone 17,21-diacetate (17652-24-3) → 21-acetoxy-11β-hydroxyl-1,4,16-pregnatriene-3,20-dione (3044-42-6) + 17α-dehydroxyprednisolone (3103-17-1)

Guidance literature:

With potassium acetate; In N-methyl-acetamide;

Reference yield: 89.3%

C23H27BrO5 → 21-acetoxy-11β-hydroxyl-1,4,16-pregnatriene-3,20-dione (3044-42-6)

Guidance literature:

With tri-n-butyl-tin hydride; benzoic acid; In acetonitrile; at 70 ℃; Inert atmosphere;

upstream raw materials:

prednisolone 17,21-diacetate

prednisolon

prednisolone Acetate

C₂₅H₃₄O₆

Downstream raw materials:

11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate

(4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-8-Benzyl-5-hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one

Acetic acid 2-((4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-8-benzyl-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester

methyl 11β,17α,21-trihydroxy-3,20-dioxo-pregna-1,4-diene-16α-carboxylate

Refernces

• 1、 -. "9-site dehalogenation method of steroid compound". Paragraph 0024. . Retrieved 2020/05/01.
• 2、 -. "Preparation method of 17a-dehydroxy prednisolone acetate". Paragraph 0027; 0030-0031; 0034; 0037-0038; 0041; 0044-0045. . Retrieved 2019/05/22.