(E)-methyl 2-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate

Base Information

• Chemical Name: (E)-methyl 2-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate
• CAS No.: 1113058-23-3
• Molecular Formula: C₁₇H₂₃NO₄
• Molecular Weight: 305.374
• Mol file: 1113058-23-3.mol

Synonyms:(E)-methyl 2-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate

Chemical Property of (E)-methyl 2-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-methyl 2-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate

There total 3 articles about (E)-methyl 2-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate 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: 96.0%

3-Boc-4-methoxycarbonyl-5-(2-phenylethyl)-cis-4,5-oxazolidin-2-one → (Z)-methyl 2-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate + (E)-methyl 2-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate (1113058-23-3)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.0833333h; stereoselective reaction; Inert atmosphere;

DOI:10.1246/bcsj.82.364

Reference yield:

3-phenyl-propionaldehyde (104-53-0) + C20H24NO7P (1438888-29-9) → (Z)-methyl 2-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate + (E)-methyl 2-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate (1113058-23-3)

Guidance literature:

C₂₀H₂₄NO₇P; With magnesium bromide ethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

3-phenyl-propionaldehyde; In tetrahydrofuran; at 20 ℃; for 17h; Overall yield = 99 %; stereoselective reaction; Inert atmosphere;

DOI:10.1002/ejoc.201300112

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → (Z)-methyl 2-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate + (E)-methyl 2-((tert-butoxycarbonyl)amino)-5-phenylpent-2-enoate (1113058-23-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: dmap / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / 2.5 h / 20 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; magnesium bromide ethyl etherate / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

3.2: 17 h / 20 °C / Inert atmosphere

With dmap; palladium 10% on activated carbon; hydrogen; magnesium bromide ethyl etherate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1002/ejoc.201300112

upstream raw materials:

di-tert-butyl dicarbonate

3-phenyl-propionaldehyde

C₂₀H₂₄NO₇P