17|A-Carboxy-17|A-formyloxy Dexamethasone

Base Information

• Chemical Name: 17|A-Carboxy-17|A-formyloxy Dexamethasone
• CAS No.: 473273-04-0
• Molecular Formula: C₂₂H₂₇FO₆
• Molecular Weight: 406.451
• UNII: 67DN63CR9Y
• DSSTox Substance ID: DTXSID80471239
• Nikkaji Number: J1.801.430K
• Wikidata: Q82299706
• Mol file: 473273-04-0.mol

Synonyms:473273-04-0;17|A-Carboxy-17|A-formyloxy Dexamethasone;17beta-Carboxy-17alpha-formyloxy Dexamethasone;67DN63CR9Y;UNII-67DN63CR9Y;(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-17-formyloxy-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthrene-17-carboxylic acid;Androsta-1,4-diene-17-carboxylic acid, 9-fluoro-17-(formyloxy)-11-hydroxy-16-methyl-3-oxo-, (11beta,16alpha,17alpha)-;17?-Carboxy-17?-formyloxy Dexamethasone;DTXSID80471239;AKOS030254412;9-Fluoro-17-(formyloxy)-11-hydroxy-16-methyl-3-oxo-(11beta,16alpha,17alpha)-androsta-1,4- diene-17-carboxylic Acid;17beta-Carboxy-17alpha-formyloxydexamethasone;17 beta -Carboxy-17 alpha -formyloxy Dexamethasone;17.BETA.-CARBOXY-17.ALPHA.-FORMYLOXY DEXAMETHASONE;(1R,2R,3AS,3BS,9AS,9BR,10S,11AS)-9B-FLUORO-1-(FORMYLOXY)-10-HYDROXY-2,9A,11A-TRIMETHYL-7-OXO-2H,3H,3AH,3BH,4H,5H,10H,11H-CYCLOPENTA[A]PHENANTHRENE-1-CARBOXYLIC ACID;ANDROSTA-1,4-DIENE-17-CARBOXYLIC ACID, 9-FLUORO-17-(FORMYLOXY)-11-HYDROXY-16-METHYL-3-OXO-, (11.BETA.,16.ALPHA.,17.ALPHA.)-

Chemical Property of 17|A-Carboxy-17|A-formyloxy Dexamethasone

Chemical Property:

• Melting Point: 228-2320C
• PSA: 100.90000
• LogP: 3.23550
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 3
• Exact Mass: 406.17916674
• Heavy Atom Count: 29
• Complexity: 850

Purity/Quality:

HPLC≥98% ^*data from raw suppliers

17β-Carboxy-17α-formyloxyDexamethasone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C(=O)O)OC=O)C)O)F)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)O)OC=O)C)O)F)C
• Uses: 17β-Carboxy-17α-formyloxy Dexamethasone is a metabolite of Dexamethasone (D298800).

Technology Process of 17|A-Carboxy-17|A-formyloxy Dexamethasone

There total 3 articles about 17|A-Carboxy-17|A-formyloxy Dexamethasone 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: 65.0%

formic acid (64-18-6) + (8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-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]phenanthrene-17-carboxylic acid (37927-01-8) → 17α-formyloxy-11β-hydroxy-9α-fluoro-16α-methyl-3-oxo-1,4-androstadien-17β-carboxylic acid (473273-04-0)

Guidance literature:

9-fluoro-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]phenanthrene-17-carboxylic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; for 1h;

formic acid; In tetrahydrofuran; water; at 15 ℃;

With triethylamine; In tetrahydrofuran; water; at 25 ℃; for 16h; Further stages.;

DOI:10.1021/jo020282g

Reference yield:

dexamethasone (50-02-2) → (8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-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]phenanthrene-17-carboxylic acid (37927-01-8) + 17α-formyloxy-11β-hydroxy-9α-fluoro-16α-methyl-3-oxo-1,4-androstadien-17β-carboxylic acid (473273-04-0) + 9α-fluoro-11β,17α-dihydroxy-16α-methyl-3,20-dioxopregna-1,4-dien-21-oic acid

Guidance literature:

dexamethasone; With copper diacetate; air; for 1.5h;

With sodium chlorite; potassium dihydrogenphosphate; 2-methyl-but-2-ene; In tetrahydrofuran; water; tert-butyl alcohol; at 25 - 40 ℃; for 16h;

DOI:10.1021/jo020282g

Reference yield:

dexamethasone (50-02-2) → 17α-formyloxy-11β-hydroxy-9α-fluoro-16α-methyl-3-oxo-1,4-androstadien-17β-carboxylic acid (473273-04-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 97 percent / H₅IO₆ / ethanol; H₂O / 16.5 h

2.1: N,N'-carbonyldiimidazole / tetrahydrofuran / 1 h

2.2: tetrahydrofuran; H₂O / 15 °C

2.3: 65 percent / triethylamine / tetrahydrofuran; H₂O / 16 h / 25 °C

With periodic acid; 1,1'-carbonyldiimidazole; In tetrahydrofuran; ethanol; water;

DOI:10.1021/jo020282g

upstream raw materials:

formic acid

(8S,9R,10S,11S,13S,14S,16R,17R)-9-fluoro-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]phenanthrene-17-carboxylic acid

dexamethasone

Refernces