(+/-)-ethyl 6-(N-tert-butoxycarbonyl)amino-3-ethoxy-6-phenylhexa-2,4-dienoate

Base Information

• Chemical Name: (+/-)-ethyl 6-(N-tert-butoxycarbonyl)amino-3-ethoxy-6-phenylhexa-2,4-dienoate
• CAS No.: 271585-83-2
• Molecular Formula: C₂₁H₂₉NO₅
• Molecular Weight: 375.465
• Mol file: 271585-83-2.mol

Synonyms:(+/-)-ethyl 6-(N-tert-butoxycarbonyl)amino-3-ethoxy-6-phenylhexa-2,4-dienoate

Chemical Property of (+/-)-ethyl 6-(N-tert-butoxycarbonyl)amino-3-ethoxy-6-phenylhexa-2,4-dienoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-ethyl 6-(N-tert-butoxycarbonyl)amino-3-ethoxy-6-phenylhexa-2,4-dienoate

There total 1 articles about (+/-)-ethyl 6-(N-tert-butoxycarbonyl)amino-3-ethoxy-6-phenylhexa-2,4-dienoate 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: 84.0%

(E)-[2-ethoxy-3-(ethoxycarbonyl)-2-propenylidene]triphenylphosphorane (145822-68-0) + 1,1-dimethyl (2-oxo-1-phenylethyl)carbamate (140196-38-9) → (+/-)-ethyl 6-(N-tert-butoxycarbonyl)amino-3-ethoxy-6-phenylhexa-2,4-dienoate (271585-83-2)

Guidance literature:

In tetrahydrofuran; at 20 ℃;

DOI:10.3987/com-99-s141

Reference yield: 90.0%

(+/-)-ethyl 6-(N-tert-butoxycarbonyl)amino-3-ethoxy-6-phenylhexa-2,4-dienoate (271585-83-2) → ethyl 1-(N-tert-butoxycarbonyl)-5-phenyl-2-pyrrolylacetate (271585-91-2)

Guidance literature:

With sulfuric acid; silica gel; In dichloromethane; at 0 ℃;

DOI:10.3987/com-99-s141

Reference yield:

(+/-)-ethyl 6-(N-tert-butoxycarbonyl)amino-3-ethoxy-6-phenylhexa-2,4-dienoate (271585-83-2) → ethyl (5-phenyl-1H-pyrrol-2-yl)acetate (220446-69-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / 97 percent concd. H₂SO₄; SiO₂ / CH₂Cl₂ / 0 °C

2: 80 percent / trifluoroacetic acid / benzene / 20 °C

With sulfuric acid; silica gel; trifluoroacetic acid; In dichloromethane; benzene; 1: cyclodehydration / 2: acidolysis;

DOI:10.3987/com-99-s141

upstream raw materials:

(E)-[2-ethoxy-3-(ethoxycarbonyl)-2-propenylidene]triphenylphosphorane

1,1-dimethyl (2-oxo-1-phenylethyl)carbamate

Downstream raw materials:

ethyl 1-(N-tert-butoxycarbonyl)-5-phenyl-2-pyrrolylacetate

ethyl (5-phenyl-1H-pyrrol-2-yl)acetate