83881-09-8

Basic information

• Product Name: MoMetasone Furoate IMpurity D
• Synonyms: MoMetasone Furoate IMpurity D;21-Chloro-17α-[(2-furanylcarbonxyl)oxy]-9β,11β-oxido-16α-Methylpregna-1,4-diene-3,20-dione;Mometasone Furoate Epoxy Impurity;21-Chloro-17α-[(2-furanylcarbonxyl)oxy]-9β-oxido-16α-methylpregna-1,4-diene-3,20-dione Mometasone Furoate Impurity D;(4aS,4bS,5aS,6aS,7R,8R,9aS,9bS)-7-(2-chloroacetyl)-4a,6a,8-trimethyl-2-oxo-2,4a,5a,6,6a,7,8,9,9a,9b,10,11-dodecahydrocyclopenta[1,2]phenanthro[4,4a-b]oxiren-7-yl furan-2-carboxylate;Mometasone Furoate EP Impurity D
• CAS NO: 83881-09-8
• Molecular Formula: C₂₇H₂₉ClO₆
• Molecular Weight: 484.96856
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 83881-09-8.mol

Chemical Properties

• Appearance: /
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), DMSO (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: MoMetasone Furoate IMpurity D(CAS DataBase Reference)
• NIST Chemistry Reference: MoMetasone Furoate IMpurity D(83881-09-8)
• EPA Substance Registry System: MoMetasone Furoate IMpurity D(83881-09-8)

Safety Data

• Hazardous Substances Data: 83881-09-8(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 83881-09-8 differently. You can refer to the following data:
1. A21-Chloro-17α-[(2-furanylcarbonxyl)oxy]-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione is a impurity of Mometasone Furoate.
2. A21-Chloro-17α-[(2-furanylcarbonxyl)oxy]-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione (Mometasone EP Impurity D) is a impurity of Mometasone Furoate.

Upstream product

• 527-69-5 2-furancarbonyl chloride 
• 83881-08-7 21-chloro-17α-hydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione 
• 24916-90-3 17α,21-dihydroxy-9β,11β-oxido-16α-methylpregna-1,4-diene-3,20-dione 

Downstream Products

• 83919-23-7 Mometasone furoate 

Relevant articles and documents

An unusual rearrangement product formed during production of mometasone furoate (Sch 32088)

The structure of an unusual rearrangement product obtained during the production of mometasone furoate (Sch 32088) was assigned on the basis of NMR and X-ray crystallography data. - Keywords: mometasone furoate; rearrangement product; mechanism; NMR data; X-ray

Preparation process of mometasone furoate

The invention relates to a chemical synthesis method of steroid drugs, in particular to a process for synthesizing mometasone furoate by a one-step method. The preparation method is characterized by comprising the following steps: mixing a compound shown in a formula 1 with liquid chloralkane, adding 4-dimethylaminopyridine under the protection of nitrogen, dropwise adding methylsulfonyl chloride at a temperature of below 5 DEG C, carrying out a stirring reaction to achieve 21-site sulfonation after dropwise adding, heating, refluxing, adding alkali, adding furfuryl chloride at a temperature of below 30 DEG C, carrying out heat preservation reaction at normal temperature, adding acetic acid and hydrochloric acid at a temperature below 25 DEG C, carrying out a 9-11-site epoxy ring-opening reaction at normal temperature, adding water after the ring-opening reaction is completed, extracting, carrying out alkali washing and water washing on an organic phase reaction solution to be neutral, layering, concentrating an organic phase, flushing with methanol/n-hexane to form crystals, and filtering to obtain mometasone furoate. According to the invention, the method effectively overcomes the defects of long original process route, complex reaction system, long consumed time and the like; and the invention provides a simpler synthesis process, which greatly shortens the synthesis route, does not need to separate and purify the compounds shown in the formulas 2 and 3, can reduce the solvent consumption and the drying time, is beneficial to energy conservation and emission reduction, and reduces the production cost.

Method for preparing mometasone furoate

The invention provides a method for preparing mometasone furoate avoiding introducing potential genotoxic impurities. According to the method, the condition is mild, and the molar yield of the whole route can be over 80 percent.

Method for synthesizing mometasone furoate or monohydrate of mometasone furoate

The invention belongs to a synthesizing method for medicine, and particularly relates to a method for synthesizing mometasone furoate or a monohydrate of the mometasone furoate. The method includes the steps that 8-DM serving as a first compound is used as an initial material, and the first compound and paratoluensulfonyl chloride are subjected to a sulfonylation reaction to generate a second compound; the second compound is not subjected to after-treatment and is subjected to a chlorination reaction with RCl (R is Li, Na, K and Et3N) to generate a third compound; the third compound is not subjected to after-treatment, a part of organic alkali is replenished, and the mixture and furoyl chloride are subjected to an esterification reaction to generate a fourth compound; the fourth compound is not subjected to after-treatment, acid adjustment is carried out, a large quantity of chlorine elements existing in a reaction system are used for a ring-opening reaction, and the mometasone furoate or the mometasone-furoate monohydrate is obtained. The method is simple in technology, mild in reaction condition, high in yield, low in cost, high in quality and raw-auxiliary-material using rate, free of genetic toxicity impurity generation and suitable for industrial production.

Unusual hydroxy-γ-sultone byproducts of steroid 21- methanesulfonylation. An efficient synthesis of mometasone 17-furoate (Sch 32088)

An efficient two stage synthesis of the steroid anti-inflammatory agent mometasone 17-furoate (Sch 32088) 4 from 17α,21-dihydroxy-16α-methyl- 9β,11β-oxidopregna-1,4-diene-3,20-dione 6 is described and the structures of unusual δ-hydroxy-γ-sultone byproducts of 4-dimethylaminopyridine catalyzed methanesulfonylation of 21-hydroxy-20-ketosteroids are deduced.