α-(N-tert-butoxycarbonyl)-β-(N-tert-butoxycarbonyl, N-propioloxy)-β-amino-L-alanine benzhydryl ester

Base Information

• Chemical Name: α-(N-tert-butoxycarbonyl)-β-(N-tert-butoxycarbonyl, N-propioloxy)-β-amino-L-alanine benzhydryl ester
• CAS No.: 158220-93-0
• Molecular Formula: C₂₉H₃₄N₂O₈
• Molecular Weight: 538.598
• Mol file: 158220-93-0.mol

Synonyms:α-(N-tert-butoxycarbonyl)-β-(N-tert-butoxycarbonyl, N-propioloxy)-β-amino-L-alanine benzhydryl ester

Chemical Property of α-(N-tert-butoxycarbonyl)-β-(N-tert-butoxycarbonyl, N-propioloxy)-β-amino-L-alanine benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of α-(N-tert-butoxycarbonyl)-β-(N-tert-butoxycarbonyl, N-propioloxy)-β-amino-L-alanine benzhydryl ester

There total 6 articles about α-(N-tert-butoxycarbonyl)-β-(N-tert-butoxycarbonyl, N-propioloxy)-β-amino-L-alanine benzhydryl 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: 91.0%

α-(N-tert-butoxycarbonyl)-β-(N-tert-butoxycarbonyl, N-hydroxy)-β-amino-L-alanine benzhydryl ester (158220-92-9) + Propiolic acid (471-25-0) → α-(N-tert-butoxycarbonyl)-β-(N-tert-butoxycarbonyl, N-propioloxy)-β-amino-L-alanine benzhydryl ester (158220-93-0)

Guidance literature:

With dicyclohexyl-carbodiimide; In dichloromethane; for 18h;

DOI:10.1016/S0040-4020(01)90416-8

Reference yield:

tert-Butyl N-hydroxycarbamate (36016-38-3) → α-(N-tert-butoxycarbonyl)-β-(N-tert-butoxycarbonyl, N-propioloxy)-β-amino-L-alanine benzhydryl ester (158220-93-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / 1-ethyl-3-<3-(dimethylamino)propyl>-carbodiimide / CH₂Cl₂ / 15 h

2: 1.) 50percent sodium hydride in mineral oil, 2.) caesium carbonate / 1.) dimethylformamide, 0 deg C, 1 h, 2.) water, dimethylformamide, 10 min

3: 93 percent / acetonitrile / 1 h

4: 91 percent / 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 18 h

With sodium hydride; caesium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dicyclohexyl-carbodiimide; In dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)90416-8

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → α-(N-tert-butoxycarbonyl)-β-(N-tert-butoxycarbonyl, N-propioloxy)-β-amino-L-alanine benzhydryl ester (158220-93-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / hydroxylamine hydrochloride, 2N aq. NaOH / dioxane / 22 h

2: 91 percent / 1-ethyl-3-<3-(dimethylamino)propyl>-carbodiimide / CH₂Cl₂ / 15 h

3: 1.) 50percent sodium hydride in mineral oil, 2.) caesium carbonate / 1.) dimethylformamide, 0 deg C, 1 h, 2.) water, dimethylformamide, 10 min

4: 93 percent / acetonitrile / 1 h

5: 91 percent / 1,3-dicyclohexylcarbodiimide / CH₂Cl₂ / 18 h

With sodium hydroxide; hydroxylamine hydrochloride; sodium hydride; caesium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; dicyclohexyl-carbodiimide; In 1,4-dioxane; dichloromethane; acetonitrile;

DOI:10.1016/S0040-4020(01)90416-8

upstream raw materials:

α-(N-tert-butoxycarbonyl)-β-(N-tert-butoxycarbonyl, N-hydroxy)-β-amino-L-alanine benzhydryl ester

Propiolic acid

tert-Butyl N-hydroxycarbamate

di-tert-butyl dicarbonate

Downstream raw materials:

β-(isoxazolin-5-on-2-yl)-L-alanine

Refernces