10106-41-9

Basic information

• Product Name: 17-alpha,21-dihydroxy-16-alpha-methylpregna-1,4,9(11)-triene-3,20-dione 21-acetate
• Synonyms: 17-alpha,21-dihydroxy-16-alpha-methylpregna-1,4,9(11)-triene-3,20-dione 21-acetate;17,21-Dihydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione 21-acetate;21-Acetyloxy-17-hydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione;17-HYDROXY-16-ALPHA-METHYL-3,20-DIOXOPREGNA-1,4,9(11)-TRIEN-21-YL ACETATE;21-Acetoxy-17-hydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione;Pregnatriene acetate;Pregna-1,4,9(11)-triene-3,20-dione, 17,21-dihydroxy-16.alpha.-methyl-, 21-acetate;2-((10S,13S,14S,16R,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate
• CAS NO: 10106-41-9
• Molecular Formula: C₂₄H₃₀O₅
• Molecular Weight: 398.492
• EINECS: 233-290-4
• Product Categories: Pharmaceuticals, Intermediates & Fine Chemicals, Steroids
• Mol File: 10106-41-9.mol
• Article Data: 13

Chemical Properties

• Melting Point: 210-213 °C
• Boiling Point: 560°Cat760mmHg
• Flash Point: 189.6°C
• Appearance: /
• Density: 1.22g/cm³
• Vapor Pressure: 7.12E-15mmHg at 25°C
• Refractive Index: 1.58
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• PKA: 12.48±0.70(Predicted)
• CAS DataBase Reference: 17-alpha,21-dihydroxy-16-alpha-methylpregna-1,4,9(11)-triene-3,20-dione 21-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 17-alpha,21-dihydroxy-16-alpha-methylpregna-1,4,9(11)-triene-3,20-dione 21-acetate(10106-41-9)
• EPA Substance Registry System: 17-alpha,21-dihydroxy-16-alpha-methylpregna-1,4,9(11)-triene-3,20-dione 21-acetate(10106-41-9)

Safety Data

• Hazardous Substances Data: 10106-41-9(Hazardous Substances Data)

Usage

Uses

17,21-Dihydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione 21-Acetate is an intermediate in the synthesis of Mometasone Furoate (M490000), a tropical corticosteroid used as an anti-inflammatory agent.

InChI:InChI=1/C24H30O5/c1-14-11-20-18-6-5-16-12-17(26)7-9-22(16,3)19(18)8-10-23(20,4)24(14,28)21(27)13-29-15(2)25/h7-9,12,14,18,20,28H,5-6,10-11,13H2,1-4H3/t14-,18-,20+,22+,23+,24+/m1/s1

Upstream product

• 50-24-8 prednisolon 
• 37413-91-5 2-((10S,13S,14S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate 
• 1201591-18-5 (Z)-2-((8S,10S,13S,14S,16R)-10,13,16-trimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-(trimethylsilyloxy)ethyl acetate 
• 6242-16-6 21-acetoxy-11α,17-dihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione 
• 78761-59-8 11α,17,21-trihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione 
• 19784-87-3 17,21-dihydroxy-16α-methyl-pregna-1,4-diene-3,20-dione 
• 7645-55-8 21-acetoxy-11α,17-dihydroxy-16α-methyl-5α-pregnane-3,20-dione 
• 115728-89-7 21-acetoxy-3β,11α,17-trihydroxy-16α-methyl-5α-pregnan-20-one 
• 96553-87-6 21-acetoxy-3β,11β,17-trihydroxy-16α-methyl-5α-pregnan-20-one 
• 96553-94-5 21-acetoxy-3β,17-dihydroxy-16α-methyl-5α-pregn-9(11)-en-20-one 
• 112835-66-2 21-bromo-3β,11α,17-trihydroxy-16α-methyl-5α-pregnan-20-one 
• 1253-34-5 21-acetoxy-3β,17-dihydroxy-16α-methyl-5α-pregnane-11,20-dione 
• 1635-20-7 3β,11α,17-trihydroxy-16α-methyl-5α-pregnan-20-one 
• 108-24-7 acetic anhydride 

Downstream Products

• 1177-87-3 betamethasone 
• 13209-41-1 (10S,13S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one 
• 83897-05-6 9α-chloro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 17-(2'-furoate) 21-acetate 
• 148596-90-1 C₂₇H₃₁ClO₇ 
• 24916-91-4 Acetic acid 2-((8S,9R,10S,11S,13S,14S,16R,17R)-9-chloro-11,17-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)-2-oxo-ethyl ester 
• 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 
• 83880-65-3 21-chloro-16α-methyl-17α-hydroxy-1,4,9(11)-pregnatriene-3,20-dione 17-(2'-furoate) 
• 912-38-9 21-acetoxy-9,11β-epoxy-17-hydroxy-16α-methyl-9β-pregna-1,4-diene-3,20-dione 

Relevant articles and documents

Expedient synthesis of 17α,21-dihydroxy-9β,11β-epoxy- 16αmethylpregna- 1,4-diene-3,20-dione 21-acetate from prednisolone utilising a novel Mattox rearrangement

A six step transformation of prednisolone to 17a,21-dihydroxy-9b,11b-epoxy- 16a-amethylpregna-1,4- diene-3,20-dione 21-acetate has been achieved in 13% unoptimised yield. Novel conditions for effecting a Mattox rearrangement and double dehydration of prednisolone were identified. Enhanced knowledge on the oxidation of silyl D19,20-enol ethers and structural factors that impact the success of the oxidation are also presented.

Improvements in corticosteroid 21-acetoxy-17α-hydroxy-16α-methyl-pregna-1,4,9(11)-triene-3,20-dione synthesis and its use as common intermediate in the synthesis of some impurities related to dexamethasone and mometasone

There are quite substantial number of impurities related to dexamethasone or mometasone which cannot be made from respective Active Pharmaceutical Ingredients but from common intermediate 21-acetoxy-17α-hydroxy-16α-methyl-pregna-1,4,9(11)-triene-3,20-dione (12). As such, a robust and economical synthesis of this key intermediate is important for delivering a resilient and economically viable supply chain for these impurities. Therefore, it is critical to have a robust and economically viable process to synthesize the intermediate 12 in good yield and quality. We report here an improved synthesis of 12 and eight impurities related to dexamethasone and mometasone from this common intermediate.

Synthesis method of 17-site side chain of steroidal drug

The invention provides a synthesis method of 17-site side chain of a steroidal drug. The method is characterized in that a compound I is taken as a starting material, and the 17-site side chain of thesteroidal drug is synthesized by means of reactions such as a nucleophilic reaction, an esterification reaction, an elimination reaction and an oxidation reaction; compared with the traditional technology, the method adopts 3-hydroxypropionitrile and a cyano group, and does not use a material such as acetone nitrile alcohol or sodium cyanide with violent toxicity, thus being safer and higher in environmental protection property; furthermore, all the steps of reactions are relatively easy to implement; the method is high in yield and purity as well as more economical and safe in production, thus being more suitable for industrial production.