(8xi,11beta,14xi,16alpha)-9,21-Dichloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl furan-2-carboxylate

Base Information

• Chemical Name: (8xi,11beta,14xi,16alpha)-9,21-Dichloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl furan-2-carboxylate
• CAS No.: 83919-23-7
• Molecular Formula: C27H30Cl2O6
• Molecular Weight: 521.438
• Hs Code.: 29372290
• NSC Number: 760077
• Mol file: 83919-23-7.mol

Synonyms:(8xi,11beta,14xi,16alpha)-9,21-dichloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl furan-2-carboxylate;Pharmakon1600-01505367;BBL031538;NSC760077;STK802011;AKOS005622580;CCG-213401;AB01563309_01

Chemical Property of (8xi,11beta,14xi,16alpha)-9,21-Dichloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl furan-2-carboxylate

Chemical Property:

• Appearance/Colour: Powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 218-220°C
• Refractive Index: 1.604
• Boiling Point: 655.5 °C at 760 mmHg
• PKA: 13.02±0.70(Predicted)
• Flash Point: 350.2 °C
• PSA: 113.02000
• Density: 1.37 g/cm³
• LogP: 6.32690
• Storage Temp.: Store at -20°C
• Solubility.: DMSO: ≥20mg/mL
• XLogP3: 3.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 520.1419441
• Heavy Atom Count: 35
• Complexity: 1020

Purity/Quality:

99%, ^*data from raw suppliers

Mometasone furoate ^*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)CCl)OC(=O)C5=CC=CO5)C)O)Cl)C
• Isomeric SMILES: C[C@@H]1CC2C3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CCl)OC(=O)C5=CC=CO5)C)O)Cl)C
• Description: Mometasone furoate is a topical steroidal antiinflammatory useful in the treatment of corticosteroid-responsive dermatoses. As a steroidal antiinflammatory of grade II potency, mometasone furoate is characterized by a once-daily dose regimen and a relatively wide safety margin.
• Uses: A topical corticosteroid used as an anti-inflammatory A deuterated topical corticosteroid used as an anti-inflammatory.;Labeled Mometasone, intended for use as an internal standard for the quantification of Mometasone by GC- or LC-mass spectrometry. Mometasone furoate has been used to study its effect on Leishmania major amastigotes.
• Biological Functions: Mometasone furoate has strong local anti-inflammatory activity equivalent to that of fluticasone propionate. It has a quick onset of action relative to the other inhaled/intranasal steroids with the least systemic availability and, consequently, the fewest systemic side effects.
• Clinical Use: Mometasone furoate was originally marketed as a topically applied corticosteroid, but because of its low systemic bioavailability, it was found to be more useful in the treatment of allergic disorders and lung diseases (107).

Technology Process of (8xi,11beta,14xi,16alpha)-9,21-Dichloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl furan-2-carboxylate

There total 17 articles about (8xi,11beta,14xi,16alpha)-9,21-Dichloro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-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: 98.2%

C27H31ClO7 (148596-90-1) → Mometasone furoate (83919-23-7,2231764-75-1)

Guidance literature:

With N-chloro-succinimide; sulfur dioxide; In dichloromethane; at 10 ℃; for 0.5h;

Reference yield: 96.0%

C28H31ClO6 → Mometasone furoate (83919-23-7,2231764-75-1)

Guidance literature:

With hydrogenchloride; acetic acid; In dichloromethane; water; at 20 - 25 ℃; for 5h;

Reference yield: 93.8%

9,11-epoxide mometasone furoate → Mometasone furoate (83919-23-7,2231764-75-1)

Guidance literature:

With hydrogenchloride; acetic acid; In water; at 5 - 25 ℃; for 9h; Temperature;

upstream raw materials:

21-chloro-16α-methyl-17α-hydroxy-1,4,9(11)-pregnatriene-3,20-dione 17-(2'-furoate)

2-furancarbonyl chloride

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

9,11-Epoxidemometasone furoate

Downstream raw materials:

Furan-2-carboxylic acid (6R,8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-17-(2-chloro-acetyl)-6,11-dihydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl ester

Refernces

• 1、 -. "Preparation process of mometasone furoate". Paragraph 0012. . Retrieved 2021/06/26.
• 2、 -. "One-pot technology for synthesizing mometasone furoate (by machine translation)". Paragraph 0022; 0024; 0028; 0029; 0033; 0034; 0038; 0039-004. . Retrieved 2020/12/31.