Kog6AE3Q8J

Base Information

• Chemical Name: Kog6AE3Q8J
• CAS No.: 25122-52-5
• Molecular Formula: C₂₅H₃₂ClFO₅
• Molecular Weight: 466.977
• UNII: KOG6AE3Q8J
• Mol file: 25122-52-5.mol

Synonyms:25122-52-5;KOG6AE3Q8J;UNII-KOG6AE3Q8J;Clobetasol propionate impurity C [EP];21-Chloro-9-fluoro-11beta-hydroxy-16alpha-methyl-3,20-dioxopregna-1,4-dien-17-yl propanoate;[(8S,9R,10S,11S,13S,14S,16R,17R)-17-(2-Chloroacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate;21-Chloro-9-fluoro-11beta,17-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 17-Propionate;Pregna-1,4-diene-3,20-dione, 21-chloro-9-fluoro-11-hydroxy-16-methyl-17-(1-oxopropoxy)-, (11beta,16alpha)-;SCHEMBL11052078;21-Chloro-9-fluoro-11|A,17-dihydroxy-16|A-methylpregna-1,4-diene-3,20-dione 17-Propionate;CLOBETASOL PROPIONATE IMPURITY C [EP IMPURITY];21-Chloro-9-fluoro-11b,17-dihydroxy-16a-methylpregna-1,4-diene-3,20-dione 17-Propionate;[(8S, 9R, 10S, 11S, 13S, 14S, 16R, 17R)-17-(2-chloroacetyl)-9-fluoro-11-hydroxy-10, 13, 16-trimethyl-3-oxo-6, 7, 8, 11, 12, 14, 15, 16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate;Pregna-1,4-diene-3,20-dione, 21-chloro-9-fluoro-11beta,17-dihydroxy-16alpha-methyl-, 17-propionate

Chemical Property of Kog6AE3Q8J

Chemical Property:

• Boiling Point: 569.0±50.0 °C(Predicted)
• PKA: 12.88±0.70(Predicted)
• PSA: 80.67000
• Density: 1.28±0.1 g/cm3(Predicted)
• LogP: 4.10310
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 466.1922300
• Heavy Atom Count: 32
• Complexity: 929

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(=O)OC1(C(CC2C1(CC(C3(C2CCC4=CC(=O)C=CC43C)F)O)C)C)C(=O)CCl
• Isomeric SMILES: CCC(=O)O[C@@]1([C@@H](C[C@@H]2[C@@]1(C[C@@H]([C@]3([C@H]2CCC4=CC(=O)C=C[C@@]43C)F)O)C)C)C(=O)CCl
• Uses: 21-Chloro-9-fluoro-11β,17-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione 17-Propionate is an impurity of Clobetasol 17-Propionate (C583500), an topical corticosteroid with anti-inflammatory properties.

Technology Process of Kog6AE3Q8J

There total 4 articles about Kog6AE3Q8J 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: 62.9%

Dexamethasone 17α,21-ethyl orthopropanoate (25122-24-1) → 21-chloro-9α-fluoro-11β-hydroxy-16α-methyl-17α-propanoyloxy-1,4-pregnadiene-3,20-dione (25122-52-5)

Guidance literature:

With phenyl chloroformate; In N,N-dimethyl-formamide; at 80 - 90 ℃; for 0.5h;

DOI:10.1248/cpb.31.12

Reference yield:

→ 21-Chlor-dexamethason-17-propionat (25122-46-7,25122-52-5)

Guidance literature:

entspr. 17,21-Butylorthopropionat;

Reference yield:

desoximetasone (382-67-2) → 21-chloro-9α-fluoro-11β-hydroxy-16α-methyl-17α-propanoyloxy-1,4-pregnadiene-3,20-dione (25122-52-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 85 percent / p-toluenesulfonic acid / dimethylformamide / 1.5 h / 85 °C

2: 58 percent / xanthene-9-carbonyl chloride / dimethylformamide / 0.5 h / 80 °C

With 9H-xanthene-9-carbonyl chloride; toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1055/s-1982-30048

upstream raw materials:

Dexamethasone 17α,21-ethyl orthopropanoate

dexamethasone

desoximetasone

Refernces

• 1、 Sugai,Okazaki,Akaboshi,et al.. "An improved synthesis of 17α-acyloxy-21-chloro-substituted corticosteroids using xanthene-9-carbonyl chloride". . p. 1023 - 1025. Retrieved 2007/10/02.