Montelukast Bis-sulfide (Mixture of Diastereomers)

Base Information

• Chemical Name: Montelukast Bis-sulfide (Mixture of Diastereomers)
• CAS No.: 1187586-61-3
• Molecular Formula: C41H46ClNO5S2
• Molecular Weight: 732.405
• Mol file: 1187586-61-3.mol

Synonyms:Montelukast Bis-sulfide (Mixture of Diastereomers);Montelukast Michael Adduct R,R-IsoMer;Montelukast Bis-sulfide;1-[[[(1R)-1-[3-[(1R)-1-[[[1-(CarboxyMethyl)cyclopropyl]Methyl]thio]-2-(7-chloro-2-quinolinyl)ethyl]phenyl]-3-[2-(1-hydroxy-1-Methylethyl)phenyl]propyl]thio]Methyl]-cyclopropaneacetic Acid;2-(1-((((R)-1-(3-((R)-1-(((1-(carboxymethyl)cyclopropyl)methyl)thio)-2-(7-chloroquinolin-2-yl)ethyl)phenyl)-3-(2-(2-hydroxypropan-2-yl)phenyl)propyl)thio)methyl)cyclopropyl)acetic acid;(R,R)-Montelukast Bis-sulfide;Montelukast Michael Adducts (mixture of diastereomers)

Chemical Property of Montelukast Bis-sulfide (Mixture of Diastereomers)

Chemical Property:

• Melting Point: 53-60°C
• Boiling Point: 856.9±65.0 °C(Predicted)
• PKA: 4.76±0.10(Predicted)
• PSA: 158.32000
• Density: 1.302±0.06 g/cm3(Predicted)
• LogP: 10.04950
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)

Purity/Quality:

97% ^*data from raw suppliers

(R,R)-MontelukastBis-sulfide(~90%) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (R,R)-Montelukast Bis-sulfide (Montelukast EP Impurity D; Montelukast USP Related Compound C) is an impurity of Montelukast and is a part of the diastereomer mixture Montelukast Bis-Sulfide (M567985). Montelukast impurity.

Technology Process of Montelukast Bis-sulfide (Mixture of Diastereomers)

There total 14 articles about Montelukast Bis-sulfide (Mixture of Diastereomers) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

1-(sulfanylmethyl)cyclopropaneacetic acid (162515-68-6) + Montelukast sodium (151767-02-1) → [R, E]-[[1-[3-[2-(7-chloro-2-quinolinyl)-2-(S)-[(carboxymethyl)cyclopropyl]methyl]thio]ethyl]phenyl]-3-[[[[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]-cyclopropane acetic acid (1187586-61-3) + [R, E]-[[1-[3-[2-(7-chloro-2-quinolinyl)-2-(R)-[(carboxymethyl)cyclopropyl]methyl]thio]ethyl]phenyl]-3-[[[[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]-cyclopropane acetic acid (1187586-58-8)

Guidance literature:

1-(sulfanylmethyl)cyclopropaneacetic acid; With sodium t-butanolate; PEG-600; In toluene; Inert atmosphere;

Montelukast sodium; In tetrahydrofuran; toluene; at 20 ℃; Inert atmosphere;

Reference yield:

C43H50ClNO5S2 → [R, E]-[[1-[3-[2-(7-chloro-2-quinolinyl)-2-(S)-[(carboxymethyl)cyclopropyl]methyl]thio]ethyl]phenyl]-3-[[[[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]-cyclopropane acetic acid (1187586-61-3) + [R, E]-[[1-[3-[2-(7-chloro-2-quinolinyl)-2-(R)-[(carboxymethyl)cyclopropyl]methyl]thio]ethyl]phenyl]-3-[[[[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]-cyclopropane acetic acid (1187586-58-8)

Guidance literature:

With water; sodium hydroxide; In methanol; at 60 - 65 ℃; for 3h;

Reference yield:

methyl 2-(3-(3-(2-(7-chloro-2-quinolinyl)ethenyl)phenyl)-3-oxopropyl)benzoate (149968-11-6) → [R, E]-[[1-[3-[2-(7-chloro-2-quinolinyl)-2-(S)-[(carboxymethyl)cyclopropyl]methyl]thio]ethyl]phenyl]-3-[[[[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]-cyclopropane acetic acid (1187586-61-3) + [R, E]-[[1-[3-[2-(7-chloro-2-quinolinyl)-2-(R)-[(carboxymethyl)cyclopropyl]methyl]thio]ethyl]phenyl]-3-[[[[2-(1-hydroxy-1-methylethyl)phenyl]propyl]thio]methyl]-cyclopropane acetic acid (1187586-58-8)

Guidance literature:

Multi-step reaction with 11 steps

1.1: (-)-diisopinocamphenylborane chloride / dichloromethane / -5 - 0 °C

2.1: cerium(III) chloride / tetrahydrofuran / 0 - 5 °C

3.1: dmap; triethylamine / dichloromethane / 0 - 5 °C

4.1: toluene-4-sulfonic acid / dichloromethane / 25 - 30 °C

5.1: water; sodium hydroxide / tetrahydrofuran; methanol / 25 - 30 °C

6.1: hydrogenchloride / water; ethyl acetate / 25 - 30 °C

7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 25 - 30 °C

7.2: 1 h / 0 - 5 °C

8.1: sodium methylate / methanol; N,N-dimethyl-formamide / 0 - 5 °C

9.1: ethyl acetate / 25 - 30 °C

10.1: sodium methylate / methanol; N,N-dimethyl-formamide / 26 h / 25 - 45 °C

11.1: sulfuric acid; water / 2.5 h / 0 - 10 °C / Inert atmosphere

With hydrogenchloride; dmap; cerium(III) chloride; sulfuric acid; water; sodium methylate; toluene-4-sulfonic acid; triethylamine; N-ethyl-N,N-diisopropylamine; (-)-diisopinocamphenylborane chloride; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; 2.1: Grignard reaction;

upstream raw materials:

1-(sulfanylmethyl)cyclopropaneacetic acid

Montelukast sodium

[R-(E)]-1-[[[1-[3-[2-(7-chloro-2-quinolinyl)ethenyl]phenyl]-3-[2-[1-(1-methyl)ethenyl]phenyl]propyl]thio]methyl]cyclopropaneacetic acid

C₄₁H₄₄ClNO₄S₂