(E)-3-[4-(tert-butoxycarbonylaminomethyl)phenyl]acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-[4-(tert-butoxycarbonylaminomethyl)phenyl]acrylic acid ethyl ester
• CAS No.: 383665-96-1
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374

Synonyms:(E)-3-[4-(tert-butoxycarbonylaminomethyl)phenyl]acrylic acid ethyl ester

Chemical Property of (E)-3-[4-(tert-butoxycarbonylaminomethyl)phenyl]acrylic acid ethyl ester

Chemical Property:

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Technology Process of (E)-3-[4-(tert-butoxycarbonylaminomethyl)phenyl]acrylic acid ethyl ester

There total 4 articles about (E)-3-[4-(tert-butoxycarbonylaminomethyl)phenyl]acrylic acid ethyl ester 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: 77.0%

tert-butyl N-(4-bromobenzyl)carbamate (68819-84-1) + ethyl acrylate (140-88-5,9003-32-1) → (E)-3-[4-(tert-butoxycarbonylaminomethyl)phenyl]acrylic acid ethyl ester (383665-96-1)

Guidance literature:

With palladium diacetate; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; propiononitrile; In N,N-dimethyl-formamide; at 90 ℃; for 6.5h; Inert atmosphere;

DOI:10.1016/j.bmc.2014.05.001

Reference yield:

2-(4-bromobenzyl)-1H-isoindole-1,3(2H)-dione (153171-22-3) → (E)-3-[4-(tert-butoxycarbonylaminomethyl)phenyl]acrylic acid ethyl ester (383665-96-1)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrazine hydrate / methanol / 1 h / Reflux

2: triethylamine / dichloromethane / 0 - 20 °C

3: palladium diacetate; propiononitrile; tris-(o-tolyl)phosphine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6.5 h / 90 °C / Inert atmosphere

With palladium diacetate; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; propiononitrile; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2014.05.001

Reference yield:

1-bromomethyl-4-bromobenzene (589-15-1) → (E)-3-[4-(tert-butoxycarbonylaminomethyl)phenyl]acrylic acid ethyl ester (383665-96-1)

Guidance literature:

Multi-step reaction with 4 steps

1: N,N-dimethyl-formamide / 6 h / 100 °C

2: hydrazine hydrate / methanol / 1 h / Reflux

3: triethylamine / dichloromethane / 0 - 20 °C

4: palladium diacetate; propiononitrile; tris-(o-tolyl)phosphine; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 6.5 h / 90 °C / Inert atmosphere

With palladium diacetate; hydrazine hydrate; triethylamine; N-ethyl-N,N-diisopropylamine; tris-(o-tolyl)phosphine; propiononitrile; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmc.2014.05.001

upstream raw materials:

1-bromomethyl-4-bromobenzene

2-(4-bromobenzyl)-1H-isoindole-1,3(2H)-dione

4-Bromobenzylamine

tert-butyl N-(4-bromobenzyl)carbamate

Downstream raw materials:

(4,4-dimethyl-3,4-dihydrocarbostyril)-6-carboxylic acid (E)-4-[2-(hydroxycarbamoyl)vinyl]benzylamide

(E)-3-[4-(4,4-dimethyl-3,4-dihydrocarbostyril-6-carbonyl)aminomethylphenyl]acrylic acid ethyl ester

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