N-(4-Methoxybenzyl)efavirenz

Base Information

• Chemical Name: N-(4-Methoxybenzyl)efavirenz
• CAS No.: 174819-21-7
• Molecular Formula: C₂₂H₁₇ClF₃NO₃
• Molecular Weight: 435.83
• UNII: BB295U888K
• DSSTox Substance ID: DTXSID00169904
• Nikkaji Number: J1.067.507C
• Wikidata: Q27274576
• Mol file: 174819-21-7.mol

Synonyms:N-(4-Methoxybenzyl)efavirenz;174819-21-7;(-)-N-(4-Methoxybenzyl)efavirenz;N-Benzylefavirenz [USP];Efavirenz impurity, N-benzylefavirenz-;UNII-BB295U888K;BB295U888K;SE 563;6-Chloro-4-(cyclopropylethynyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one, (S)-;(4S)-6-chloro-4-(2-cyclopropylethynyl)-1-[(4-methoxyphenyl)methyl]-4-(trifluoromethyl)-3,1-benzoxazin-2-one;(S)-6-Chloro-4-(cyclopropylethynyl)-1-(4-methoxybenzyl)-4-(trifluoromethyl)-2H-3,1-benzoxazin-2-one;2H-3,1-Benzoxazin-2-one, 6-chloro-4-(2-cyclopropylethynyl)-1,4-dihydro-1-((4-methoxyphenyl)methyl)-4-(trifluoromethyl)-, (4S)-;EFAVIRENZ IMPURITY D;SCHEMBL12828992;DTXSID00169904;BKYROQXKHLSLOS-NRFANRHFSA-N;SE-563;N-BENZYLEFAVIRENZ [USP IMPURITY];J-011044;Q27274576;(4S)-1-(4-Methoxybenzyl)-4alpha-(trifluoromethyl)-4-(cyclopropylethynyl)-6-chloro-1,4-dihydro-2H-3,1-benzoxazine-2-one

Chemical Property of N-(4-Methoxybenzyl)efavirenz

Chemical Property:

• Melting Point: 112-114°C
• XLogP3: 5.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 435.0849056
• Heavy Atom Count: 30
• Complexity: 720

Purity/Quality:

97% ^*data from raw suppliers

SE563 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=C(C=C1)CN2C3=C(C=C(C=C3)Cl)C(OC2=O)(C#CC4CC4)C(F)(F)F
• Isomeric SMILES: COC1=CC=C(C=C1)CN2C3=C(C=C(C=C3)Cl)[C@@](OC2=O)(C#CC4CC4)C(F)(F)F
• Uses: SE 563 is used in the synthesis of an HIV-1 reverse trancriptase inhibitor, Efavirenz (E425000).

Technology Process of N-(4-Methoxybenzyl)efavirenz

There total 6 articles about N-(4-Methoxybenzyl)efavirenz 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: 96.0%

phosgene (75-44-5) + (S)-5-chloro-α-(cyclopropylethynyl)-2-<<(4-methoxyphenyl)methyl>amino>-α-(trifluoromethyl)benzenemethanol (173676-60-3) → (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-1-<(4'-methoxyphenyl)methyl>-3,1-benzoxazin-2-one (174819-21-7)

Guidance literature:

With potassium carbonate; In tetrahydrofuran;

DOI:10.1016/0040-4039(95)01955-H

Reference yield: 91.0%

(S)-5-chloro-α-(cyclopropylethynyl)-2-<<(4-methoxyphenyl)methyl>amino>-α-(trifluoromethyl)benzenemethanol (173676-60-3) + 5-chloro-α-(cyclopropylethynyl)-2-<(triphenylmethyl)amino>-α-(trifluoromethyl)benzenemethanol → (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-1-<(4'-methoxyphenyl)methyl>-3,1-benzoxazin-2-one (174819-21-7)

Guidance literature:

With triethylamine; In toluene; for 1h;

DOI:10.1021/jo981170l

Reference yield:

1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone (154598-53-5) → (S)-6-chloro-4-(cyclopropylethynyl)-1,4-dihydro-4-(trifluoromethyl)-1-<(4'-methoxyphenyl)methyl>-3,1-benzoxazin-2-one (174819-21-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 2 h / Heating

2: 1.) (1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide, triphenylmethane / 1.) THF, toluene, hexanes, 0-5 deg C, 30 min, 2.) THF, toluene, hexanes, -55 deg C, 60 min

3: 91 percent / triethylamine / toluene / 1 h

With triphenylmethane; (1R,2S)-N-pyrrolidinylnorephedrine lithium alkoxide; toluene-4-sulfonic acid; triethylamine; In toluene; acetonitrile;

DOI:10.1021/jo981170l

upstream raw materials:

phosgene

(S)-5-chloro-α-(cyclopropylethynyl)-2-<<(4-methoxyphenyl)methyl>amino>-α-(trifluoromethyl)benzenemethanol

4-Methoxybenzyl alcohol

1-(2-amino-5-chloro-phenyl)-2,2,2-trifluoro-ethanone

Downstream raw materials:

efavirenz

Refernces

• 1、 Thompson, Andrew S.,Corley, Edward G.,Huntington, Martha F.,Grabowski, E. J. J.. "Use of an Ephedrine Alkoxide to Mediate Enantioselective Addition of an Acetylide to a Prochiral Ketone: Asymmetric Synthesis of the Reverse Transcriptase Inhibitor L-743,726.". . p. 8937 - 8940. Retrieved 2007/10/02.