184764-13-4

Basic information

• Product Name: 1-[2-[(3S)-3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]phenyl]acetate
• Synonyms: 1-[2-[(3S)-3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]phenyl]acetate;[S-(E)]-1-[2-[3-[3-[2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]phenyl]ethanone;1-{2-[(3S)-3-{3-[(E)-2-(7-Chloro-2-quinolinyl)vinyl]phenyl}-3-hydroxypropyl]phenyl}ethanone;Montelukast (3S)-Hydroxy Methylketone
• CAS NO: 184764-13-4
• Molecular Formula: C₂₈H₂₄ClNO₂
• Molecular Weight: 457.94806
• Product Categories: Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 184764-13-4.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 637.553 °C at 760 mmHg
• Flash Point: 339.38 °C
• Appearance: Yellow Solid
• Density: 1.256 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.692
• Storage Temp.: Refrigerator
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 14.07±0.20(Predicted)
• CAS DataBase Reference: 1-[2-[(3S)-3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]phenyl]acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-[2-[(3S)-3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]phenyl]acetate(184764-13-4)
• EPA Substance Registry System: 1-[2-[(3S)-3-[3-[(1E)-2-(7-Chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl]phenyl]acetate(184764-13-4)

Safety Data

• Hazardous Substances Data: 184764-13-4(Hazardous Substances Data)

Usage

Chemical Properties

Yellow Solid

Uses

Intermediate in the production of Montelukast metabolites

InChI:InChI=1/C28H24ClNO2/c1-19(31)26-8-3-2-6-21(26)12-16-28(32)23-7-4-5-20(17-23)9-14-25-15-11-22-10-13-24(29)18-27(22)30-25/h2-11,13-15,17-18,28,32H,12,16H2,1H3/b14-9+/t28-/m0/s1

Upstream product

• 181139-72-0 methyl-[(E)]-2-[3(S)-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-hydroxypropyl] benzoate 
• 149968-11-6 methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxopropyl)benzoate 
• 676-58-4 methylmagnesium chloride 

Downstream Products

• 937275-23-5 [R,E]-1-[[[1-[3-[2-(7-chloro-2-quinolinyl) ethenyl]phenyl]-3-[2-(methylcarbonyl)phenyl] propyl]thio]methyl]cyclopropane acetic acid 
• 151767-02-1 Montelukast sodium 
• 158966-92-8 montelukast 
• 1013023-56-7 (S)-(E)-1-(2-(1-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-1-(methanesulfonyl-oxy)propyl)phenyl)ethanone 
• 213380-36-0 (S)-2-(3-[3-(2-(7-chloro-2-quinolinyl)-(E)-ethenyl)phenyl]-3-tert-butyldimethylsilyloxypropyl)ethanone 
• 184764-27-0 (1-{(R)-1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-3-[2-(1-hydroxy-2-methoxymethoxy-1-methyl-ethyl)-phenyl]-propylsulfanylmethyl}-cyclopropyl)-acetic acid 
• 186353-01-5 Methanesulfonic acid (S)-1-{3-[(E)-2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-[2-(1-hydroxy-2-methoxymethoxy-1-methyl-ethyl)-phenyl]-propyl ester 
• 184764-20-3 (S)-1-{3-[(E)-2-(7-Chloro-quinolin-2-yl)-vinyl]-phenyl}-3-[2-(1-hydroxy-2-methoxymethoxy-1-methyl-ethyl)-phenyl]-propan-1-ol 

Relevant articles and documents

Insights into the cerium chloride-catalyzed grignard addition to esters

Addition of methylmagnesium chloride to ester 1 in the presence of cerium chloride gave significantly better yields of the tertiary alcohol 2 than the reaction performed in the absence of cerium chloride. The beneficial effect of added cerium chloride is postulated to be due to suppression of the enolization of the ketone intermediate. The use of properly activated anhydrous cerium chloride which is proposed to generate a less basic, more nucleophilic species to overcome this undesired reaction was found to be critical. The activated cerium chloride was identified as the known seven-coordinate THF solvate, [CeCl(μ-Cl)2(THF)2]n. Inactive crystal forms were also identified and the key parameters for formation of the active form were delineated.

PROCESS FOR THE PREPARATION OF MONTELUKAST, AND INTERMEDIATES THEREFOR

The invention relates to processes for making montelukast and to intermediates for use in the process, in particular compounds of formulas 2-7: L=OAc, OTs, OTf5OMs; where X=Cl, Br, I.