2-(N-tert-butoxycarbonyl)-4-[N-(2-chlorobenzyloxycarbonyl)-N-methoxy]-2,4-diaminobutanoic acid

Base Information

• Chemical Name: 2-(N-tert-butoxycarbonyl)-4-[N-(2-chlorobenzyloxycarbonyl)-N-methoxy]-2,4-diaminobutanoic acid
• CAS No.: 620590-46-7
• Molecular Formula: C₁₈H₂₅ClN₂O₇
• Molecular Weight: 416.859
• Mol file: 620590-46-7.mol

Synonyms:2-(N-tert-butoxycarbonyl)-4-[N-(2-chlorobenzyloxycarbonyl)-N-methoxy]-2,4-diaminobutanoic acid

Chemical Property of 2-(N-tert-butoxycarbonyl)-4-[N-(2-chlorobenzyloxycarbonyl)-N-methoxy]-2,4-diaminobutanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-(N-tert-butoxycarbonyl)-4-[N-(2-chlorobenzyloxycarbonyl)-N-methoxy]-2,4-diaminobutanoic acid

There total 6 articles about 2-(N-tert-butoxycarbonyl)-4-[N-(2-chlorobenzyloxycarbonyl)-N-methoxy]-2,4-diaminobutanoic acid 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: 85.0%

allyl 2-(N-tert-butoxycarbonyl)amino-4-bromobutanoate (475150-36-8) + N-(2-chlorobenzyloxycarbonyl)methoxylamine (620590-49-0) → 2-(N-tert-butoxycarbonyl)-4-[N-(2-chlorobenzyloxycarbonyl)-N-methoxy]-2,4-diaminobutanoic acid (620590-46-7)

Guidance literature:

allyl 2-(N-tert-butoxycarbonyl)amino-4-bromobutanoate; N-(2-chlorobenzyloxycarbonyl)methoxylamine; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.0583333h;

With pyrrolidine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; for 1.5h;

DOI:10.1021/jo034984x

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → 2-(N-tert-butoxycarbonyl)-4-[N-(2-chlorobenzyloxycarbonyl)-N-methoxy]-2,4-diaminobutanoic acid (620590-46-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaOH / H₂O; acetonitrile / 14 h

2.1: 1.40 g / dimethylformamide / 19 h

3.1: Et₃N / CH₂Cl₂ / 1.58 h

4.1: 2.34 g / LiBr / CH₂Cl₂; acetone / 14 h

5.1: NaH / dimethylformamide / 0.06 h / 0 °C

5.2: 85 percent / Ph₃P; pyrrolidine / Pd(PPh₃)4 / CH₂Cl₂ / 1.5 h

With sodium hydroxide; sodium hydride; triethylamine; lithium bromide; In dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1021/jo034984x

Reference yield:

L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid (41088-86-2) → 2-(N-tert-butoxycarbonyl)-4-[N-(2-chlorobenzyloxycarbonyl)-N-methoxy]-2,4-diaminobutanoic acid (620590-46-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1.40 g / dimethylformamide / 19 h

2.1: Et₃N / CH₂Cl₂ / 1.58 h

3.1: 2.34 g / LiBr / CH₂Cl₂; acetone / 14 h

4.1: NaH / dimethylformamide / 0.06 h / 0 °C

4.2: 85 percent / Ph₃P; pyrrolidine / Pd(PPh₃)4 / CH₂Cl₂ / 1.5 h

With sodium hydride; triethylamine; lithium bromide; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo034984x

upstream raw materials:

allyl 2-(N-tert-butoxycarbonyl)amino-4-bromobutanoate

N-(2-chlorobenzyloxycarbonyl)methoxylamine

di-tert-butyl dicarbonate

L-2-(tert-butyloxycarbonylamino)-4-hydroxybutyric acid

Refernces