151265-36-0

Basic information

• Product Name: (16α)-21-Chloro-17-hydroxy-16-Methylpregna-1,4,9(11)-triene-3,20-dione
• Synonyms: (16α)-21-Chloro-17-hydroxy-16-Methylpregna-1,4,9(11)-triene-3,20-dione
• CAS NO: 151265-36-0
• Molecular Formula: C22H27ClO3
• Molecular Weight: 374.9
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 151265-36-0.mol

Chemical Properties

• Boiling Point: 535.1±50.0 °C(Predicted)
• Appearance: /
• Density: 1.24±0.1 g/cm3(Predicted)
• PKA: 12.43±0.70(Predicted)
• CAS DataBase Reference: (16α)-21-Chloro-17-hydroxy-16-Methylpregna-1,4,9(11)-triene-3,20-dione(CAS DataBase Reference)
• NIST Chemistry Reference: (16α)-21-Chloro-17-hydroxy-16-Methylpregna-1,4,9(11)-triene-3,20-dione(151265-36-0)
• EPA Substance Registry System: (16α)-21-Chloro-17-hydroxy-16-Methylpregna-1,4,9(11)-triene-3,20-dione(151265-36-0)

Safety Data

• Hazardous Substances Data: 151265-36-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(16α)-21-Chloro-17-hydroxy-16-Methylpregna-1,4,9(11)-triene-3,20-dione is used as an intermediate in the synthesis of Mometasone Furoate (M490000), a topical corticosteroid. It serves as a key component in the production process, enabling the creation of an anti-inflammatory agent that can be applied to treat various skin conditions, such as eczema, dermatitis, and other inflammatory skin disorders.
Application Reason:
The compound's unique structure allows it to be a vital building block in the synthesis of Mometasone Furoate, which is known for its potent anti-inflammatory properties. By acting as an intermediate, (16α)-21-Chloro-17-hydroxy-16-Methylpregna-1,4,9(11)-triene-3,20-dione contributes to the development of an effective treatment for skin inflammation and other related conditions.

Upstream product

• 13209-41-1 (8S,10S,13S,14S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-3-one 
• 124-63-0 methanesulfonyl chloride 
• 898-84-0 11α-hydroxy-androsta-1,4-diene-3,17-dione 

Relevant articles and documents

An effective method for the preparation of 21-chlorosteroids using the Vilsmeier reagent

A simple procedure for the conversion of 21-steroidal alcohols to the corresponding 12-chlorides using the Vilsmeier reagent is described.

Preparation method of mometasone furoate

The invention relates to the technical field of chemical pharmacy, in particular to a preparation method of mometasone furoate. The preparation method comprises the following steps: carrying out a cyanohydrination reaction on a compound I to obtain a compound II, carrying out an alkylation reaction on the compound II to obtain a compound III, carrying out an intramolecular substitution reaction on the compound III to obtain a compound IV, carrying out a furfurylation reaction on the compound IV to obtain a compound V, and finally carrying out a chlorohydroxyl reaction on the compound V to obtain mometasone furoate. The mometasone furoate is obtained by adopting the compound I through the cyanohydrination reaction, the alkylation reaction, the intramolecular substitution reaction, the furfurylation reaction and the chlorohydroxyl reaction, the quality and the yield of the obtained mometasone furoate have obvious competitiveness, the quality yield is high, the purity is high, the purity reaches 99.20% or above, and the content of any impurity is smaller than 0.10%. The preparation method of mometasone furoate provided by the invention adopts the easily prepared compound I as the raw material, and is low in cost, green and environment-friendly.

Preparation method of clobetasol propionate

The invention provides a brand new synthesis route for preparation of clobetasol propionate; adopted raw materials are cheaper and are easier to obtain, reactive raw materials are hydroxylated and then chloridized, carbonyl protection groups are removed, five-membered ring double bonds are subjected to selective oxidation and reduction, after esterification, six-membered ring double bonds are subjected to epoxidation, and then fluorination ring opening is performed to obtain the clobetasol propionate product. The reaction process is easy to operate, the yield of each step is relatively high, the purity of the obtained product is higher, the formation of by-products is effectively avoided, the production cost is reduced and industrialized production is facilitated.

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.

17β-cyano-9α,17α-dihydroxyandrost-4-en-3-one

The invention is the compound 17β-cyano-9α, 17α-dihydroxyandrost-4-en-3-one (I) which is particularly useful as an intermediate in the production of the 17α-halo silyl ethers (II).