L-Proline, N-[3-(4-hydroxyphenyl)-1-oxopropyl]-L-isoleucyl-, 2-[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]ethyl ester

Base Information

• Chemical Name: L-Proline, N-[3-(4-hydroxyphenyl)-1-oxopropyl]-L-isoleucyl-, 2-[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]ethyl ester
• CAS No.: 658053-32-8
• Molecular Formula: C31H48N4O7
• Molecular Weight: 588.745
• Mol file: 658053-32-8.mol

Synonyms:

Chemical Property of L-Proline, N-[3-(4-hydroxyphenyl)-1-oxopropyl]-L-isoleucyl-, 2-[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of L-Proline, N-[3-(4-hydroxyphenyl)-1-oxopropyl]-L-isoleucyl-, 2-[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]ethyl ester

There total 8 articles about L-Proline, N-[3-(4-hydroxyphenyl)-1-oxopropyl]-L-isoleucyl-, 2-[4-[(1,1-dimethylethoxy)carbonyl]-1-piperazinyl]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: 55.0%

tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate (77279-24-4) + N-[3-(4-hydroxyphenyl)propionyl]-L-isoleucyl-L-proline (658053-31-7) → N-[3-(4-hydroxyphenyl)propionyl]-L-isoleucyl-L-proline 2-[4-(tert-butyloxycarbonyl)piperazin-1-yl]ethyl ester (658053-32-8)

Guidance literature:

N-[3-(4-hydroxyphenyl)propionyl]-L-isoleucyl-L-proline; With diisopropyl-carbodiimide; In dichloromethane; for 1h;

tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate; In dichloromethane; at 20 ℃;

DOI:10.1007/s00706-003-0007-3

Reference yield:

1-(2-hydroxyethyl)piperazine (103-76-4) → N-[3-(4-hydroxyphenyl)propionyl]-L-isoleucyl-L-proline 2-[4-(tert-butyloxycarbonyl)piperazin-1-yl]ethyl ester (658053-32-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 96 percent / CH₂Cl₂ / 0 °C

2.1: diisopropylcarbodiimide / CH₂Cl₂ / 1 h / cooling

2.2: 55 percent / CH₂Cl₂ / 20 °C

With diisopropyl-carbodiimide; In dichloromethane;

DOI:10.1002/ardp.200300726

Reference yield:

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) → N-[3-(4-hydroxyphenyl)propionyl]-L-isoleucyl-L-proline 2-[4-(tert-butyloxycarbonyl)piperazin-1-yl]ethyl ester (658053-32-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: aq. Na₂CO₃ / 0.25 h

1.2: 73 percent / dicyclohexylcarbodiimide / ethyl acetate / 16 h / 0 - 20 °C

2.1: trifluoroacetic acid / CH₂Cl₂ / 3 h / 20 °C

2.2: diisopropylethylamine / CH₂Cl₂

3.1: 48 percent / ethanol / 20 °C

4.1: 1.87 g / aq. LiOH / 1,2-dimethoxy-ethane / 2 h / 20 °C

5.1: diisopropylcarbodiimide / CH₂Cl₂ / 1 h / cooling

5.2: 55 percent / CH₂Cl₂ / 20 °C

With lithium hydroxide; sodium carbonate; trifluoroacetic acid; diisopropyl-carbodiimide; In 1,2-dimethoxyethane; ethanol; dichloromethane;

DOI:10.1002/ardp.200300726

upstream raw materials:

tert-butyl 4-(2-hydroxyethyl)piperazine-1-carboxylate

N-[3-(4-hydroxyphenyl)propionyl]-L-isoleucyl-L-proline

1-(2-hydroxyethyl)piperazine

N-(tert-butyloxycarbonyl)-L-isoleucine