Naloxegol

Base Information

• Chemical Name: Naloxegol
• CAS No.: 854601-70-0
• Molecular Formula: C34H53NO11
• Molecular Weight: 651.78472
• Mol file: 854601-70-0.mol

Synonyms:Naloxegol;Movantik

Chemical Property of Naloxegol

Chemical Property:

• Boiling Point: 730.6±60.0 °C(Predicted)
• PKA: 9.36±0.60(Predicted)
• PSA: 126.77000
• Density: 1.25±0.1 g/cm3(Predicted)
• LogP: 1.80140

Purity/Quality:

99% ^*data from raw suppliers

Naloxegol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Naloxegol is a peripherally-selective opioid antagonist.

Technology Process of Naloxegol

There total 18 articles about Naloxegol 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:

(4R,4aS,7aR,12bS)-7-(2,5,8,11,14,17,20-heptaoxadocosan-22-yloxy)-3-allyl-9-((2-methoxyethoxy)methoxy)-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-ol → (5α,6α)-17-allyl-6-(2,5,8,11,14,17,20-heptaoxadocosan-22-yloxy)-4,5-epoxymorphinan-3,14-diol (854601-70-0)

Guidance literature:

(4R,4aS,7aR,12bS)-7-(2,5,8,11,14,17,20-heptaoxadocosan-22-yloxy)-3-allyl-9-((2-methoxyethoxy)methoxy)-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-4a-ol; With hydrogenchloride; 2,6-di-tert-butyl-4-methyl-phenol; In ethyl acetate; at 10 - 15 ℃; for 1.5h;

With sodium carbonate; In water;

Reference yield:

C41H59NO11 → (5α,6α)-17-allyl-6-(2,5,8,11,14,17,20-heptaoxadocosan-22-yloxy)-4,5-epoxymorphinan-3,14-diol (854601-70-0)

Guidance literature:

C₄₁H₅₉NO₁₁; With titanium tetrachloride; In dichloromethane; at 25 - 30 ℃; for 2h;

With water; In dichloromethane;

Reference yield:

triethylene glucol monomethyl ether (112-35-6,95507-80-5) → (5α,6α)-17-allyl-6-(2,5,8,11,14,17,20-heptaoxadocosan-22-yloxy)-4,5-epoxymorphinan-3,14-diol (854601-70-0)

Guidance literature:

Multi-step reaction with 8 steps

1.1: triethylamine / dichloromethane / 1 h / 0 - 30 °C

2.1: potassium hydroxide / tetrahydrofuran / 0.5 h / 60 - 70 °C

2.2: 24 h / Reflux

3.1: hydrogenchloride; pyrographite; palladium 10% on activated carbon; hydrogen / water; ethanol / 4 h / Autoclave

4.1: triethylamine / dichloromethane / 1.5 h / 0 - 30 °C

5.1: tetrabutylammomium bromide / toluene / 2 h / 20 - 85 °C

6.1: sodium hydride / toluene; N,N-dimethyl-formamide / 1 h / 5 - 10 °C / Inert atmosphere

6.2: 8 - 16 °C / Inert atmosphere

6.3: 15 - 20 °C

7.1: sodium carbonate / dichloromethane; water / 0.33 h / 20 - 30 °C

8.1: hydrogenchloride; 2,6-di-tert-butyl-4-methyl-phenol / ethyl acetate / 1.5 h / 10 - 15 °C

With hydrogenchloride; 2,6-di-tert-butyl-4-methyl-phenol; palladium 10% on activated carbon; tetrabutylammomium bromide; hydrogen; sodium hydride; sodium carbonate; pyrographite; triethylamine; potassium hydroxide; In tetrahydrofuran; ethanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

upstream raw materials:

(4R,4aS,7aR,12bS)-3-allyl-9-((2-methoxyethoxy)methoxy)-2,3,4,4a,5,6,7,7a-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-4a,7-diol

22-bromo-2,5,8,11,14,17,20-heptaoxadocosane

triethylene glucol monomethyl ether

8-methoxy-1-(methylsulfonyl)oxy-3,6-dioxaoctane

Downstream raw materials:

naloxegol oxalate

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF (5Α,6Α)-17-ALLYL-6-(2,5,8,11,14,17,20- HEPTAOXADOCOSAN-22-YLOXY)-4,5-EPOXYMORPHINAN-3,14-DIOL AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS". . . Retrieved 2019/04/16.