10-Oxo-3-O-methylnaltrexone

Base Information

• Chemical Name: 10-Oxo-3-O-methylnaltrexone
• CAS No.: 96445-13-5
• Molecular Formula: C21H23NO5
• Molecular Weight: 369.41102
• DSSTox Substance ID: DTXSID30461786
• Nikkaji Number: J2.046.160H
• Wikidata: Q82286202
• Mol file: 96445-13-5.mol

Synonyms:10-Oxo-3-O-methylnaltrexone;96445-13-5;10-Oxo Naltrexone Methyl Ether;(4S,4aS,7aR,12bS)-3-(cyclopropylmethyl)-4a-hydroxy-9-methoxy-1,2,4,5,6,7a-hexahydro-4,12-methanobenzofuro[3,2-e]isoquinoline-7,13-dione;DTXSID30461786

Chemical Property of 10-Oxo-3-O-methylnaltrexone

Chemical Property:

• Melting Point: 90-95°C
• PSA: 76.07000
• LogP: 1.40650
• Storage Temp.: Refrigerator
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 3
• Exact Mass: 369.15762283
• Heavy Atom Count: 27
• Complexity: 707

Purity/Quality:

99.0% Min ^*data from raw suppliers

10-Oxo Naltrexone Methyl Ether ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C2C3=C(C=C1)C(=O)C4C5(C3(CCN4CC6CC6)C(O2)C(=O)CC5)O
• Isomeric SMILES: COC1=C2C3=C(C=C1)C(=O)[C@@H]4[C@]5([C@]3(CCN4CC6CC6)[C@@H](O2)C(=O)CC5)O
• Uses: Naltrexone derivative, showing significantly less potency than pure Naltrexone.

Technology Process of 10-Oxo-3-O-methylnaltrexone

There total 5 articles about 10-Oxo-3-O-methylnaltrexone 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: 4.6%

naltrexone methyl ether (16617-07-5) → 10-hydroxynaltrexone 3-methyl ether (96445-12-4) + 17-(cyclopropylmethyl)-4,5α-epoxy-14β-hydroxy-3-methoxymorphinan-6,10-dione (96445-13-5)

Guidance literature:

With chromium(VI) oxide; sulfuric acid; at 25 ℃; for 28h;

DOI:10.1021/jm00145a024

Reference yield:

10-hydroxynaltrexone 3-methyl ether (96445-12-4) → 17-(cyclopropylmethyl)-4,5α-epoxy-14β-hydroxy-3-methoxymorphinan-6,10-dione (96445-13-5)

Guidance literature:

With CrO₃-DMP; In dichloromethane; for 0.25h;

DOI:10.1021/jm00145a024

Reference yield:

naltrexone methyl ether (16617-07-5) → 17-(cyclopropylmethyl)-4,5α-epoxy-14β-hydroxy-3-methoxymorphinan-6,10-dione (96445-13-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 4.6 percent / CrO₃, conc. H₂SO₄ / 28 h / 25 °C

2: 9.2 mg / CrO₃-DMP complex / CH₂Cl₂ / 0.25 h

With chromium(VI) oxide; CrO₃-DMP; sulfuric acid; In dichloromethane;

DOI:10.1021/jm00145a024

upstream raw materials:

naltrexone methyl ether

10-hydroxynaltrexone 3-methyl ether

cyclopropylcarbinyl bromide

C₂₄H₂₉NO₈

Downstream raw materials:

10-Ketonaltrexone

6β-(N-benzyl)methylamino-17-(cyclopropylmethyl)-4,5α-epoxy-14β-hydroxy-3-methoxymorphinan-10-one

6β-(N-benzyl)methylamino-17-(cyclopropylmethyl)-4,5α-epoxy-3,14β-dihydroxymorphinan-10-one