5-((E)-2-(tetrahydro-2H-pyran-2-yloxycarbamoyl)vinyl)-N-benzyl-2-methylbenzamide

Base Information

• Chemical Name: 5-((E)-2-(tetrahydro-2H-pyran-2-yloxycarbamoyl)vinyl)-N-benzyl-2-methylbenzamide
• CAS No.: 914647-76-0
• Molecular Formula: C₂₃H₂₆N₂O₄
• Molecular Weight: 394.47

Synonyms:5-((E)-2-(tetrahydro-2H-pyran-2-yloxycarbamoyl)vinyl)-N-benzyl-2-methylbenzamide

Chemical Property of 5-((E)-2-(tetrahydro-2H-pyran-2-yloxycarbamoyl)vinyl)-N-benzyl-2-methylbenzamide

Chemical Property:

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Technology Process of 5-((E)-2-(tetrahydro-2H-pyran-2-yloxycarbamoyl)vinyl)-N-benzyl-2-methylbenzamide

There total 6 articles about 5-((E)-2-(tetrahydro-2H-pyran-2-yloxycarbamoyl)vinyl)-N-benzyl-2-methylbenzamide 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: 52.0%

(E)-3-(3-(benzylcarbamoyl)-4-methylphenyl)acrylic acid (914647-75-9) + O-2-tetrahydro-2H-pyranhydroxylamine (6723-30-4) → 5-((E)-2-(tetrahydro-2H-pyran-2-yloxycarbamoyl)vinyl)-N-benzyl-2-methylbenzamide (914647-76-0)

Guidance literature:

(E)-3-(3-(benzylcarbamoyl)-4-methylphenyl)acrylic acid; With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at 0 ℃;

O-2-tetrahydro-2H-pyranhydroxylamine; In tetrahydrofuran; at 20 ℃;

DOI:10.1016/j.bmc.2006.07.008

Reference yield:

5-nitro-o-toluic acid (1975-52-6) → 5-((E)-2-(tetrahydro-2H-pyran-2-yloxycarbamoyl)vinyl)-N-benzyl-2-methylbenzamide (914647-76-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine; ethyl chloroformate / tetrahydrofuran / 1 h / 0 °C

1.2: 70 percent / tetrahydrofuran

2.1: 91 percent / hydrogen / Pd-C / ethyl acetate / 2 h / 20 °C

3.1: hydrobromic acid; sodium nitrite / methanol; acetone / cooling

3.2: 85 percent / Cu₂O / methanol; acetone / 35 - 40 °C

4.1: 100 percent / 1,5-diazabicyclo[5.4.0]undec-5-ene / toluene / Heating

5.1: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 20 °C

6.1: ethyl chloroformate; triethylamine / tetrahydrofuran / 0 °C

6.2: 52 percent / tetrahydrofuran / 20 °C

With hydrogen bromide; hydrogen; chloroformic acid ethyl ester; triethylamine; trifluoroacetic acid; 1,5-Diazabicyclo[5.4.0]undec-5-ene; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetone; toluene;

DOI:10.1016/j.bmc.2006.07.008

Reference yield:

benzylamine (100-46-9) → 5-((E)-2-(tetrahydro-2H-pyran-2-yloxycarbamoyl)vinyl)-N-benzyl-2-methylbenzamide (914647-76-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triethylamine; ethyl chloroformate / tetrahydrofuran / 1 h / 0 °C

1.2: 70 percent / tetrahydrofuran

2.1: 91 percent / hydrogen / Pd-C / ethyl acetate / 2 h / 20 °C

3.1: hydrobromic acid; sodium nitrite / methanol; acetone / cooling

3.2: 85 percent / Cu₂O / methanol; acetone / 35 - 40 °C

4.1: 100 percent / 1,5-diazabicyclo[5.4.0]undec-5-ene / toluene / Heating

5.1: 100 percent / trifluoroacetic acid / CH₂Cl₂ / 20 °C

6.1: ethyl chloroformate; triethylamine / tetrahydrofuran / 0 °C

6.2: 52 percent / tetrahydrofuran / 20 °C

With hydrogen bromide; hydrogen; chloroformic acid ethyl ester; triethylamine; trifluoroacetic acid; 1,5-Diazabicyclo[5.4.0]undec-5-ene; sodium nitrite; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; acetone; toluene;

DOI:10.1016/j.bmc.2006.07.008

upstream raw materials:

(E)-3-(3-(benzylcarbamoyl)-4-methylphenyl)acrylic acid

O-2-tetrahydro-2H-pyranhydroxylamine

(E)-tert-butyl 3-(3-(benzylcarbamoyl)-4-methylphenyl)acrylate

tert-butyl 3-(3-(benzylcarbamoyl)-4-methylphenyl)-2-bromopropanoate

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