5-((tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic pentafluorophenol ester

Base Information

• Chemical Name: 5-((tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic pentafluorophenol ester
• CAS No.: 1333912-05-2
• Molecular Formula: C₁₇H₁₈F₅NO₅
• Molecular Weight: 411.326
• Mol file: 1333912-05-2.mol

Synonyms:5-((tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic pentafluorophenol ester

Chemical Property of 5-((tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic pentafluorophenol ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-((tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic pentafluorophenol ester

There total 5 articles about 5-((tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic pentafluorophenol 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: 83.0%

2,3,4,5,6-pentafluorophenol (771-61-9) + 5-((tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic acid (1333911-91-3) → 5-((tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic pentafluorophenol ester (1333912-05-2)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In ethyl acetate; at 0 - 20 ℃; for 25h; Inert atmosphere;

DOI:10.1016/j.tetlet.2011.07.078

Reference yield:

3-(tert-butyloxycarbonylamino)propionic acid (3303-84-2) → 5-((tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic pentafluorophenol ester (1333912-05-2)

Guidance literature:

Multi-step reaction with 5 steps

1: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 3.5 h / 0 - 20 °C / Inert atmosphere

2: 5 h / Inert atmosphere; Reflux

3: potassium carbonate / acetone / 24 h / 20 °C / Inert atmosphere

4: water; lithium hydroxide / tetrahydrofuran / 43 h / 20 - 50 °C / Inert atmosphere

5: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / ethyl acetate / 25 h / 0 - 20 °C / Inert atmosphere

With dmap; water; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hydroxide; In tetrahydrofuran; dichloromethane; ethyl acetate; acetone;

DOI:10.1016/j.tetlet.2011.07.078

Reference yield:

[3-(2,2-dimethyl-4,6-dioxo-[1,3]-dioxan-5-yl)-3-oxo-propyl]-carbamic acid tert-butyl ester → 5-((tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic pentafluorophenol ester (1333912-05-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 5 h / Inert atmosphere; Reflux

2: potassium carbonate / acetone / 24 h / 20 °C / Inert atmosphere

3: water; lithium hydroxide / tetrahydrofuran / 43 h / 20 - 50 °C / Inert atmosphere

4: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / ethyl acetate / 25 h / 0 - 20 °C / Inert atmosphere

With dmap; water; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium hydroxide; In tetrahydrofuran; ethyl acetate; acetone;

DOI:10.1016/j.tetlet.2011.07.078

upstream raw materials:

5-((tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic acid methyl ester

2,3,4,5,6-pentafluorophenol

5-((tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic acid

3-(tert-butyloxycarbonylamino)propionic acid

Downstream raw materials:

5-(di(tert-butoxycarbonyl)amino)-3-methoxypent-2-enoic pentafluorophenol ester