8-Hydroxyefavirenz

Base Information

• Chemical Name: 8-Hydroxyefavirenz
• CAS No.: 205754-33-2
• Molecular Formula: C₁₄H₉ClF₃NO₃
• Molecular Weight: 331.679
• UNII: P8S49CKH6L
• DSSTox Substance ID: DTXSID50942769
• Nikkaji Number: J1.525.087I
• ChEMBL ID: CHEMBL1309
• Mol file: 205754-33-2.mol

Synonyms:6-chloro-4-(cyclopropylethynyl)-8-hydroxy-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one;8-hydroxy-efavirenz;8-hydroxy-efavirenz-glucuronide;8-hydroxyefavirenz

Chemical Property of 8-Hydroxyefavirenz

Chemical Property:

• Melting Point: 144-154°C
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 1
• Exact Mass: 331.0223053
• Heavy Atom Count: 22
• Complexity: 551

Purity/Quality:

99% ^*data from raw suppliers

rac 8-Hydroxy Efavirenz ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC1C#CC2(C3=C(C(=CC(=C3)Cl)O)NC(=O)O2)C(F)(F)F
• Isomeric SMILES: C1CC1C#C[C@]2(C3=C(C(=CC(=C3)Cl)O)NC(=O)O2)C(F)(F)F
• Description: 8-hydroxy Efavirenz is a major oxidative metabolite of the non-nucleoside reverse transcriptase inhibitor efavirenz . 8-hydroxy Efavirenz is formed when efavirenz is metabolized by the cytochrome P450 (CYP) isoform CYP2B6. It induces apoptosis in rat primary hippocampal neurons and loss of dendritic spines in rat primary hippocampal neuronal cultures when used at a concentration of 0.01 μM.
• Uses: A labellebed metabolite of Efavirenz, a nonnucleoside HIV-1 reverse transcriptase inhibitor 8-Hydroxy Efavirenz is a metabolite of Efavirenz (E425000), a nonnucleoside HIV-1 reverse transcriptase inhibitor.

Technology Process of 8-Hydroxyefavirenz

There total 13 articles about 8-Hydroxyefavirenz 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: 80.0%

8-mesyloxy-efavirenz → 8-Hydroxyefavirenz (205754-33-2,342621-26-5,205754-32-1)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere; Schlenk technique;

DOI:10.1021/jacs.8b09208

Reference yield: 9.5%

efavirenz (154598-52-4,154635-17-3) → 8-Hydroxyefavirenz (205754-33-2,342621-26-5,205754-32-1)

Guidance literature:

With N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamineiron(II) bis(triflate); dihydrogen peroxide; acetic acid; In ethyl acetate; acetonitrile; at 40 ℃; for 72h;

DOI:10.1039/c2ob25212k

Reference yield:

efavirenz (154598-52-4,154635-17-3) → 7-Hydroxyefavirenz + 8-Hydroxyefavirenz (205754-33-2,342621-26-5,205754-32-1)

Guidance literature:

With N,N'-dimethyl-N,N'-bis(2-pyridylmethyl)ethane-1,2-diamineiron(II) bis(triflate); dihydrogen peroxide; acetic acid; In ethyl acetate; acetonitrile; at 40 ℃; for 72h;

DOI:10.1039/c2ob25212k

upstream raw materials:

8-(tert-butyl-dimethyl-silanyloxy)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

1-chloro-3-methoxy-4-nitrobenzene

4-chloro-o-anisidine

N-(4-chloro-2-methoxyphenyl)-2,2-dimethylpropanamide

Refernces

• 1、 Harjivan, Shrika G.,Wanke, Riccardo,Ferreira Da Silva, Jo?o L.,Marques, M. Matilde,Antunes, Alexandra M.M.. "The phenolic metabolites of the anti-HIV drug efavirenz: Evidence for distinct reactivities upon oxidation with Fre?my's salt". . p. 7 - 11. Retrieved 2014/02/14.
• 2、 Wanke, Riccardo,Novais, David A.,Harjivan, Shrika G.,Marques, M. Matilde,Antunes, Alexandra M. M.. "Biomimetic oxidation of aromatic xenobiotics: Synthesis of the phenolic metabolites from the anti-HIV drug efavirenz". experimental part. p. 4554 - 4561. Retrieved 2012/08/08.