8-(tert-Butyldimethylsilyloxy) 8-Hydroxy Efavirenz, Technical Grade

Base Information

• Chemical Name: 8-(tert-Butyldimethylsilyloxy) 8-Hydroxy Efavirenz, Technical Grade
• CAS No.: 1027042-31-4
• Molecular Formula: C₂₀H₂₃ClF₃NO₃Si
• Molecular Weight: 445.941
• DSSTox Substance ID: DTXSID30449887
• Mol file: 1027042-31-4.mol

Synonyms:1027042-31-4;8-(tert-Butyldimethylsilyloxy) 8-Hydroxy Efavirenz, Technical Grade;8-(tert-Butyldimethylsilyloxy) 8-Hydroxy Efavirenz;8-[tert-butyl(dimethyl)silyl]oxy-6-chloro-4-(2-cyclopropylethynyl)-4-(trifluoromethyl)-1H-3,1-benzoxazin-2-one;DTXSID30449887;SFKCIHFYAYBXNU-UHFFFAOYSA-N;FT-0664032;8-(tert-Butyldimethylsilyloxy)8-hydroxy efavirenz,technical grade;8-{[tert-Butyl(dimethyl)silyl]oxy}-6-chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-3,1-benzoxazin-2-one

Chemical Property of 8-(tert-Butyldimethylsilyloxy) 8-Hydroxy Efavirenz, Technical Grade

Chemical Property:

• Melting Point: 133-135?C
• PSA: 51.05000
• LogP: 5.90630
• Storage Temp.: Refrigerator
• Solubility.: Chloroform, Dichloromethane, Dimethyl Sulfoxide, Methanol
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 445.1087823
• Heavy Atom Count: 29
• Complexity: 735

Purity/Quality:

98%Min ^*data from raw suppliers

8-(tert-Butyldimethylsilyloxy)8-HydroxyEfavirenz,TechnicalGrade ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)(C)[Si](C)(C)OC1=CC(=CC2=C1NC(=O)OC2(C#CC3CC3)C(F)(F)F)Cl
• Uses: Efavirenz (E425000) intermediate. Efavirenz intermediate.

Technology Process of 8-(tert-Butyldimethylsilyloxy) 8-Hydroxy Efavirenz, Technical Grade

There total 8 articles about 8-(tert-Butyldimethylsilyloxy) 8-Hydroxy Efavirenz, Technical Grade 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:

phosgene (75-44-5) + 2-(2-Amino-5-chloro-3-(t-butyldimethylsilyloxy)-phenyl)-4-cyclopropyl-1,1,1-trifluoro-3-butyn-2-ol (205756-25-8) → 8-(tert-butyl-dimethyl-silanyloxy)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (1027042-31-4)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In toluene; at -25 - 20 ℃;

DOI:10.1016/S0960-894X(01)00012-9

Reference yield:

1-chloro-3-methoxy-4-nitrobenzene (6627-53-8) → 8-(tert-butyl-dimethyl-silanyloxy)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (1027042-31-4)

Guidance literature:

Multi-step reaction with 8 steps

1: SnCl₂; EtOH / Heating

2: NEt₃ / CH₂Cl₂

3: s-BuLi / tetrahydrofuran / -20 - 0 °C

4: aq. HCl / 1,2-dimethoxy-ethane / Heating

5: BBr₃ / CH₂Cl₂

6: imidazole / dimethylformamide / 0 °C

7: 76 percent / tetrahydrofuran; hexane / -20 °C

8: i-Pr₂NEt / toluene / -25 - 20 °C

With 1H-imidazole; hydrogenchloride; ethanol; sec.-butyllithium; boron tribromide; triethylamine; N-ethyl-N,N-diisopropylamine; tin(ll) chloride; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0960-894X(01)00012-9

Reference yield:

4-chloro-o-anisidine (93-50-5) → 8-(tert-butyl-dimethyl-silanyloxy)-6-chloro-4-cyclopropylethynyl-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one (1027042-31-4)

Guidance literature:

Multi-step reaction with 7 steps

1: NEt₃ / CH₂Cl₂

2: s-BuLi / tetrahydrofuran / -20 - 0 °C

3: aq. HCl / 1,2-dimethoxy-ethane / Heating

4: BBr₃ / CH₂Cl₂

5: imidazole / dimethylformamide / 0 °C

6: 76 percent / tetrahydrofuran; hexane / -20 °C

7: i-Pr₂NEt / toluene / -25 - 20 °C

With 1H-imidazole; hydrogenchloride; sec.-butyllithium; boron tribromide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1016/S0960-894X(01)00012-9

upstream raw materials:

phosgene

2-(2-Amino-5-chloro-3-(t-butyldimethylsilyloxy)-phenyl)-4-cyclopropyl-1,1,1-trifluoro-3-butyn-2-ol

1-chloro-3-methoxy-4-nitrobenzene

4-chloro-o-anisidine

Downstream raw materials:

8-Hydroxyefavirenz

6-chloro-4-cyclopropylethynyl-8-hydroxy-4-trifluoromethyl-1,4-dihydro-benzo[d][1,3]oxazin-2-one

Refernces