21172-43-0

Basic information

• Product Name: Methanesulfonic acid 3-(3-trifluoroMethylphenyl)propyl ester
• Synonyms: Methanesulfonic acid 3-(3-trifluoroMethylphenyl)propyl ester;Cinacalcet Impurity 14
• CAS NO: 21172-43-0
• Molecular Formula: C₁₁H₁₃F₃O₃S
• Molecular Weight: 282.2793296
• Mol File: 21172-43-0.mol

Chemical Properties

• Boiling Point: 365.9±42.0 °C(Predicted)
• Appearance: /
• Density: 1.305±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, Refrigerator, under inert atmosphere
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• CAS DataBase Reference: Methanesulfonic acid 3-(3-trifluoroMethylphenyl)propyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Methanesulfonic acid 3-(3-trifluoroMethylphenyl)propyl ester(21172-43-0)
• EPA Substance Registry System: Methanesulfonic acid 3-(3-trifluoroMethylphenyl)propyl ester(21172-43-0)

Safety Data

• Hazardous Substances Data: 21172-43-0(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Methanesulfonic acid 3-(3-trifluoroMethylphenyl)propyl ester is used as an impurity in the production of Cinacalcet (C441800) for the treatment of secondary hyperparathyroidism. Its presence in the drug formulation is essential for understanding the safety and efficacy of the medication, as it may contribute to potential side effects or interactions with other compounds.
As an impurity in Cinacalcet, Methanesulfonic acid 3-(3-trifluoroMethylphenyl)propyl ester plays a role in the overall pharmacological profile of the drug. It is crucial to monitor and control the levels of this impurity to ensure the safety and effectiveness of Cinacalcet in treating elevated parathyroid hormone levels.

Upstream product

• 294856-02-3 methyl 3-(3-(trifluoromethyl)phenyl)propanoate 
• 585-50-2 3-(3-trifluoromethylphenyl)propanoic acid 
• 21172-41-8 3-[3-(trifluoromethyl)phenyl]propanal 
• 78573-45-2 3-[3-(trifluoromethyl)phenyl]propan-1-ol 
• 124-63-0 methanesulfonyl chloride 

Downstream Products

• 364782-34-3 cinacalcet hydrochloride 
• 226256-56-0 cinacalcet 
• 1206633-34-2 C₂₃H₂₄F₃N 
• 1204313-94-9 C₃₃H₃₁F₆NO₂ 
• 1204313-91-6 (R)-tert-butyl (1-(naphthalen-1-yl)ethyl)(3-(3-(trifluoromethyl)phenyl)propyl)carbamate 

Relevant articles and documents

Cinacalcet hydrochloride preparation method

The invention provides a cinacalcet hydrochloride preparation method, wherein the cinacalcet hydrochloride finished product is obtained by using 3-(3-trifluoromethylphenyl)propanol and (R)-(+)-1-(1-naphthyl)ethylamine as starting raw materials through two-step chemical reaction, one-step salt formation and two-step purification. According to the present invention, the method has characteristics ofsimple process, easily-available raw materials, economy and environmental protection, easily achieves industrialization, and can promote the economic and technological development of cinacalcet hydrochloride bulk drugs.

Method for preparing cinacalcet hydrochloride

The invention provides a method for preparing cinacalcet hydrochloride. The method comprises the following steps: with 3-(3-trifluoromethylphenyl)propanol shown as a formula I as a starting material,performing an acylation reaction on the starting material and methylsulfonyl chloride to obtain methylsulfonyl-3-(3-trifluoromethylphenyl) propyl ester shown as a formula II; in the presence of K2CO3,KI and ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate, performing a substitution reaction on the methylsulfonyl-3-(3-trifluoromethylphenyl) propyl ester shown as the formula II and (R)-1-(1-naphthyl)ethylamine shown as a formula III to obtain a system containing a compound shown as a formula IV; performing a salt forming reaction on the compound shown as the formula IV and hydrochloric acid to obtain a target product, namely the cinacalcet hydrochloride. Through the addition of the trace KI and the ionic liquid 1-butyl-3-methylimidazolium trifluoromethanesulfonate in the substitution reaction in the step 2), the substitution reaction is speeded up, the yield of the product is increased and the purity of the product is improved.

Method for synthesizing calcimimetic cinacalcet hydrochloride

The invention provides a method for synthesizing calcimimetic cinacalcet hydrochloride; the method comprises the steps of preparing methylsulfonyl-3-(3-trifluoromethylphenyl)propionate; preparing (R)-(+)-1-(1-naphthyl)ethyltribenzyllamine; preparing N-((1R)-1-(1-napthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propyl-1-tribenzylamine; preparing N-((1R)-1-(1-napthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propylamine hydrochloride. The synthetic route of the method has the advantages of low price and easy access of materials, good operational simplicity, high yield and the like.

Preparation method of high-purity m-trifluoromethyl phenylpropanol methanesulfonate

The invention belongs to the field of medicine preparation, and particularly relates to a preparation method of high-purity m-trifluoromethyl phenylpropanol methanesulfonate. The preparation method comprises the following steps of using m-trifluoromethyl phenylpropanol as the raw material, using methylsulfonyl chloride as an acylating agent, using triethylamine as an acid-binding agent, using dichloromethane as a solvent, and reacting; after reaction is finished, adding water to hydrolyze, standing and delaminating, drying and filtering an organic layer, and concentrating filtrate, so as to obtain the high-purity m-trifluoromethyl phenylpropanol methanesulfonate. The purity of the high-purity m-trifluoromethyl phenylpropanol methanesulfonate reaches 99.2% or above, the yield rate reaches 95% or above, and the prepared product can meet the requirement of medicine registration. The preparation method has the advantages that the production of impurities can be reduced by the reaction temperature, reaction time, and solvent removal by pressure-relief concentration, so as to improve the purity; the obtaining of raw materials is easy, the technology is reasonable, and the prepared sample can meet the requirement of medicine registration.

Metal-Free Enantioselective Oxidative Arylation of Alkenes: Hypervalent-Iodine-Promoted Oxidative C?C Bond Formation

The enantioselective oxyarylation of (E)-6-aryl-1-silyloxylhex-3-ene was achieved using a lactate-based chiral hypervalent iodine(III) reagent in the presence of boron trifluoride diethyl etherate. The silyl ether promotes the oxidative cyclization, and enhances the enantioselectivity. In addition, the corresponding aminoarylation was achieved.

PROCESS FOR PREPARING CINACALCET AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

The resent invention rovides a novel rocess for re arin cinacalcet of formula I and pharmaceutically acceptable salts thereof and process of purification. The present invention also provides novel nitrogen protected synthetic intermediates useful in the process of the present invention. Further, the present invention provides a novel substituted carbamate impurity and process of preparation thereof.

PROCESS FOR THE PREPARATION OF CINACALCET AND SALTS THEREOF, AND INTERMEDIATES FOR USE IN THE PROCESS

There is provided a process for preparing a salt of the (R)- or (S)-isomer of 1- naphthylethylamine with mandelic acid or a derivative thereof, the process comprising reacting racemic 1-naphthylethylamine with mandelic acid or a derivative thereof to obtain the (R)- or (S)-isomer of 1-naphthylethylamine salt (III) with the acid. The salts also form an aspect of the present invention. There is also provided a salt of the (R)- or (S)-isomer of 1-naphthylethylamine with mandelic acid or a derivative thereof. There is also provided a process for preparing cinacalcet (I) or a salt thereof, the process comprising reacting an ester (II) with (R)-i-naphthylethylamine or a salt of (R)-i-naphthylethylamine and mandelic acid or a derivative thereof, to obtain cinacalcet, and optionally converting the cincalcet to a salt thereof.

PROCESS FOR PREPARING CINACALCET AND PHARMACEUTICALLY ACCEPTABLE SALTS THEREOF

The resent invention rovides a novel rocess for re arin cinacalcet of formula I and pharmaceutically acceptable salts thereof and process of purification. The present invention also provides novel nitrogen protected synthetic intermediates useful in the process of the present invention. Further, the present invention provides a novel substituted carbamate impurity and process of preparation thereof.

Disubstituted imidazoles useful in the treatment of bacterial infections

Novel disubstituted imidazoles are disclosed which are useful in the treatment of bacterial infections, particularly through the inhibition of FAB I.