Naltrexone 14-acetate

Base Information

• Chemical Name: Naltrexone 14-acetate
• CAS No.: 121962-99-0
• Molecular Formula: C₂₂H₂₅NO₅
• Molecular Weight: 383.444
• DSSTox Substance ID: DTXSID30153452
• Nikkaji Number: J274.608E
• Wikidata: Q83020327
• Mol file: 121962-99-0.mol

Synonyms:Naltrexone 14-acetate;14-O-Acetylnaltrexone;121962-99-0;Morphinan-6-one, 14-(acetyloxy)-17-(cyclopropylmethyl)-4,5-epoxy-3-hydroxy-, (5alpha)-;DTXSID30153452

Chemical Property of Naltrexone 14-acetate

Chemical Property:

• Vapor Pressure: 7.71E-13mmHg at 25°C
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 383.17327290
• Heavy Atom Count: 28
• Complexity: 722

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(=O)OC12CCC(=O)C3C14CCN(C2CC5=C4C(=C(C=C5)O)O3)CC6CC6
• Isomeric SMILES: CC(=O)O[C@@]12CCC(=O)[C@H]3[C@@]14CCN([C@@H]2CC5=C4C(=C(C=C5)O)O3)CC6CC6

Technology Process of Naltrexone 14-acetate

There total 4 articles about Naltrexone 14-acetate 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: 79.0%

4,5α-epoxy-3,14-diacetoxy-6-oxo-17-(cyclopropylmethyl)morphinan (92398-19-1) → 14-Acetoxy-17-(cyclopropylmethyl)-3-hydroxy-6-oxo-4,5α-epoxymorphinan (121962-99-0)

Guidance literature:

With sulfuric acid; for 24h; Ambient temperature;

DOI:10.1016/0223-5234(94)90125-2

Reference yield: 62.0%

naltrexone Hydrochloride (16676-29-2) + acetic anhydride (108-24-7) → 14-Acetoxy-17-(cyclopropylmethyl)-3-hydroxy-6-oxo-4,5α-epoxymorphinan (121962-99-0)

Guidance literature:

Heating;

DOI:10.1021/jo00288a068

Reference yield:

Naltrexone (16590-41-3) → 14-Acetoxy-17-(cyclopropylmethyl)-3-hydroxy-6-oxo-4,5α-epoxymorphinan (121962-99-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 83 percent / 1 h / Heating

2: 79 percent / 4percent aq. H₂SO₄ / 24 h / Ambient temperature

With sulfuric acid;

DOI:10.1016/0223-5234(94)90125-2

upstream raw materials:

naltrexone Hydrochloride

acetic anhydride

Naltrexone

4,5α-epoxy-3,14-diacetoxy-6-oxo-17-(cyclopropylmethyl)morphinan