O-tert-Butyl-2-hydroxy Efavirenz

Base Information

• Chemical Name: O-tert-Butyl-2-hydroxy Efavirenz
• CAS No.: 201218-08-8
• Molecular Formula: C₁₈H₁₉ClF₃NO₃
• Molecular Weight: 389.802
• DSSTox Substance ID: DTXSID001109508
• Mol file: 201218-08-8.mol

Synonyms:201218-08-8;tert-butyl N-[4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl]carbamate;O-tert-Butyl-2-hydroxy Efavirenz;GHCJVKSQWMFUFL-UHFFFAOYSA-N;DTXSID001109508;1,1-Dimethylethyl N-[4-chloro-2-[3-cyclopropyl-1-hydroxy-1-(trifluoromethyl)-2-propyn-1-yl]phenyl]carbamate;tert-butyl N-[4-chloro-2-(4-cyclopropyl-1, 1, 1-trifluoro-2-hydroxybut-3-yn-2-yl)phenyl]carbamate

Chemical Property of O-tert-Butyl-2-hydroxy Efavirenz

Chemical Property:

• XLogP3: 5.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 5
• Exact Mass: 389.1005556
• Heavy Atom Count: 26
• Complexity: 600

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)NC1=C(C=C(C=C1)Cl)C(C#CC2CC2)(C(F)(F)F)O

Technology Process of O-tert-Butyl-2-hydroxy Efavirenz

There total 2 articles about O-tert-Butyl-2-hydroxy 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: 94.0%

tert-butyl 4-chloro-2-(7-chloro-1,1,1-trifluoro-2-hydroxyhept-3-yn-2-yl)phenylcarbamate (202721-01-5) → tert-butyl 4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenylcarbamate (201218-08-8)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at -40 - -5 ℃; for 3h; Inert atmosphere;

Reference yield: 65.0%

tert-butyl-4-chloro-2-(2,2,2-trifluoroacetyl)phenyl carbamate (201218-07-7) + 1-chloro-4-pentyne (14267-92-6) → tert-butyl 4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenylcarbamate (201218-08-8)

Guidance literature:

1-chloro-4-pentyne; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -5 - 0 ℃; for 2.16667h;

tert-butyl-4-chloro-2-(2,2,2-trifluoroacetyl)phenyl carbamate; In tetrahydrofuran; hexane; at -35 ℃; for 1.75h;

Reference yield: 95.0%

tert-butyl 4-chloro-2-(4-cyclopropyl-1,1,1-trifluoro-2-hydroxybut-3-yn-2-yl)phenylcarbamate (201218-08-8) → rac-efavirenz (177530-93-7,154635-17-3)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; toluene; at 0 ℃; for 1h; Inert atmosphere; Reflux;

upstream raw materials:

tert-butyl-4-chloro-2-(2,2,2-trifluoroacetyl)phenyl carbamate

1-chloro-4-pentyne

tert-butyl 4-chloro-2-(7-chloro-1,1,1-trifluoro-2-hydroxyhept-3-yn-2-yl)phenylcarbamate

Downstream raw materials:

rac-efavirenz