[(8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-17-(2,2-dioxo-5H-oxathiol-4-yl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] furan-2-carboxylate

Base Information

• Chemical Name: [(8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-17-(2,2-dioxo-5H-oxathiol-4-yl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] furan-2-carboxylate
• CAS No.: 223776-49-6
• Molecular Formula: C₂₈H₃₁ClO₈S
• Molecular Weight: 563.068
• UNII: 8MZU56S9QP
• Mol file: 223776-49-6.mol

Synonyms:223776-49-6;8MZU56S9QP;[(8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-17-(2,2-dioxo-5H-oxathiol-4-yl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] furan-2-carboxylate;Mometasone EP Impurity B;UNII-8MZU56S9QP;Mometasone furoate impurity B [EP];MOMETASONE FUROATE IMPURITY B [EP IMPURITY];(11.BETA.,16.ALPHA.,17.ALPHA.)-9-CHLORO-17-(2,2-DIOXIDO-5H-1,2-OXATHIOL-4-YL)-17-((2-FURANYLCARBONYL)OXY)-11-HYDROXY-16-METHYLANDROSTA-1,4-DIEN-3-ONE;(11b,16a,17a)-9-Chloro-17-(2,2-dioxido-5H-1,2-oxathiol-4-yl)-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-methyl-androsta-1,4-dien-3-one;(11beta,16alpha,17alpha)-9-Chloro-17-(2,2-dioxido-5H-1,2-oxathiol-4-yl)-17-((2-furanylcarbonyl)oxy)-11-hydroxy-16-methylandrosta-1,4-dien-3-one;(11Beta,16Alpha,17Alpha)-9-Chloro-17-(2,2-dioxido-5H-1,2-oxathiol-4-yl)-17-[(2-furanylcarbonyl)oxy]-;(11Beta,16Alpha,17Alpha)-9-Chloro-17-(2,2-dioxido-5H-1,2-oxathiol-4-yl)-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-methyl-androsta-1,4-dien-3-one Mometasone Furoate Impurity B;4-[9-Chloro-17-[(furan-2-yl-carbonyl)oxy]-11beta-hydroxy-16alpha-methyl-3-oxoandrosta-1,4-dien-17beta-yl]-5H-1,2-oxathiole 2,2-Dioxide;9-CHLORO-17.BETA.-(2,2-DIOXO-2,5-DIHYDRO-1,2.LAMBDA.6-OXATHIOL-4-YL)-11.BETA.-HYDROXY-16.ALPHA.-METHYL-3-OXOANDROSTA-1,4-DIEN-17.ALPHA.-YL FURAN-2-CARBOXYLATE;9-Chloro-17beta-(2,2-dioxo-2,5-dihydro-1,2lambda6-oxathiol-4-yl)-11beta-hydroxy-16alpha-methyl-3-oxoandrosta-1,4-dien-17alpha-yl furan-2-carboxylate;ANDROSTA-1,4-DIEN-3-ONE, 9-CHLORO-17-(2,2-DIOXIDO-5H-1,2-OXATHIOL-4-YL)-17-((2-FURANYLCARBONYL)OXY)-11-HYDROXY-16-METHYL-, (11.BETA.,16.ALPHA.,17.ALPHA.)-;Androsta-1,4-dien-3-one, 9-chloro-17-(2,2-dioxido-5H-1,2-oxathiol-4-yl)-17-((2-furanylcarbonyl)oxy)-11-hydroxy-16-methyl-, (11beta,16alpha,17alpha)-;Androsta-1,4-dien-3-one, 9-chloro-17-(2,2-dioxido-5H-1,2-oxathiol-4-yl)-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-methyl-, (11?,16?,17?)-;(11?,16?,17?)-9-Chloro-17-(2,2-dioxido-5H-1,2-oxathiol-4-yl)-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-methylandrosta-1,4-dien-3-one;Mometasone Furoate Imp. B (EP)

Chemical Property of [(8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-17-(2,2-dioxo-5H-oxathiol-4-yl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] furan-2-carboxylate

Chemical Property:

• Melting Point: >145°C (dec.)
• Storage Temp.: Amber Vial, -20°C Freezer, Under inert atmosphere
• Solubility.: Chloroform, Methanol (Slightly)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 4
• Exact Mass: 562.1428168
• Heavy Atom Count: 38
• Complexity: 1280

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C3(C(CC2(C1(C5=CS(=O)(=O)OC5)OC(=O)C6=CC=CO6)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(C5=CS(=O)(=O)OC5)OC(=O)C6=CC=CO6)C)O)Cl)C
• Uses: As impurity of Mometasone Furoate, (11β,16α,17α)-9-Chloro-17-(2,2-dioxido-5H-1,2-oxathiol-4-yl)-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-Methyl-androsta-1,4-dien-3-one can be used as a topical corticosteroid used as an anti-inflammatory. (11β,16α,17α)-9-Chloro-17-(2,2-dioxido-5H-1,2-oxathiol-4-yl)-17-[(2-furanylcarbonyl)oxy]-11-hydroxy-16-methyl-androsta-1,4-dien-3-one (Mometasone EP Impurity B) is an impurity of Mometasone Furoate, a topical corticosteroid used as an anti-inflammatory.

Technology Process of [(8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-17-(2,2-dioxo-5H-oxathiol-4-yl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] furan-2-carboxylate

There total 4 articles about [(8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-17-(2,2-dioxo-5H-oxathiol-4-yl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] furan-2-carboxylate 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: 87.0%

17β-(2,2-dioxido-3,4-dehydro-1,2-oxathiolan-4-yl)-9β,11β-epoxy-17α-hydroxy-16α-methylandrosta-1,4-dien-3-one 17-(2-furoate) (223776-50-9) → 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) (223776-49-6)

Guidance literature:

With hydrogenchloride; In acetic acid; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(98)01146-6

Reference yield:

17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione (24916-90-3) → 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) (223776-49-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.1 percent / 4-DMAP, CH₃SO₂Cl / CH₂Cl₂ / 4 h / Heating

2: 10 mg / 4-DMAP, Et₃N / CH₂Cl₂ / 5 h / Ambient temperature

3: 87 percent / conc. HCl / acetic acid / 2 h / Ambient temperature

With hydrogenchloride; dmap; methanesulfonyl chloride; triethylamine; In dichloromethane; acetic acid;

DOI:10.1016/S0040-4020(98)01146-6

Reference yield:

2-furancarbonyl chloride (527-69-5) → 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) (223776-49-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 10 mg / 4-DMAP, Et₃N / CH₂Cl₂ / 5 h / Ambient temperature

2: 87 percent / conc. HCl / acetic acid / 2 h / Ambient temperature

With hydrogenchloride; dmap; triethylamine; In dichloromethane; acetic acid;

DOI:10.1016/S0040-4020(98)01146-6

upstream raw materials:

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

2-furancarbonyl chloride

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

9β,11β-epoxy-17α-hydroxy-17β-(4-(R)-hydroxy-2,2-dioxido-1,2-oxathiolan-4-yl)-16α-methylandrosta-1,4-diene-3-one

Refernces