ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate

Base Information

• Chemical Name: ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate
• CAS No.: 908254-64-8
• Molecular Formula: C₂₅H₂₆ClNO₄
• Molecular Weight: 439.939
• Mol file: 908254-64-8.mol

Synonyms:ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate

Chemical Property of ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate

There total 4 articles about ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate 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: 57.0%

ethyl 4-isopropyl-6-(4-chlorophenyl)-4-(trimethylsiloxy)-(5E)-hexen-2-ynoate (908254-39-7) + O-benzyl carbamate (621-84-1) → ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate (908254-64-8)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 ℃; for 0.5h;

DOI:10.1021/ol0616485

Reference yield:

(E)-6-(4-Chloro-phenyl)-4-hydroxy-4-isopropyl-hex-5-en-2-ynoic acid ethyl ester → ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate (908254-64-8)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / tetrahydrofuran / 0.5 h / 20 °C

2: 57 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / -30 °C

With 1H-imidazole; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol0616485

Reference yield:

(E)-1-(4-chlorophenyl)-4-methylpent-1-en-3-one (67962-15-6) → ethyl 6-(N-benzyloxycarbonyl)amino-4-isopropyl-6-(4-chlorophenyl)-(4Z)-hexen-2-ynoate (908254-64-8)

Guidance literature:

Multi-step reaction with 3 steps

1: BuLi / hexane; tetrahydrofuran / 4.5 h / -78 - 0 °C

2: imidazole / tetrahydrofuran / 0.5 h / 20 °C

3: 57 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / -30 °C

With 1H-imidazole; n-butyllithium; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ol0616485

upstream raw materials:

ethyl 4-isopropyl-6-(4-chlorophenyl)-4-(trimethylsiloxy)-(5E)-hexen-2-ynoate

O-benzyl carbamate

(E)-1-(4-chlorophenyl)-4-methylpent-1-en-3-one

propynoic acid ethyl ester