methyl (2S,3S)-2-{4'-[(4-aminophenyl)buta-1',3'-diynyl]benzamido}-3-hydroxybutanoate

Base Information

• Chemical Name: methyl (2S,3S)-2-{4'-[(4-aminophenyl)buta-1',3'-diynyl]benzamido}-3-hydroxybutanoate
• CAS No.: 1276668-07-5
• Molecular Formula: C₂₂H₂₀N₂O₄
• Molecular Weight: 376.412
• Mol file: 1276668-07-5.mol

Synonyms:methyl (2S,3S)-2-{4'-[(4-aminophenyl)buta-1',3'-diynyl]benzamido}-3-hydroxybutanoate

Chemical Property of methyl (2S,3S)-2-{4'-[(4-aminophenyl)buta-1',3'-diynyl]benzamido}-3-hydroxybutanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2S,3S)-2-{4'-[(4-aminophenyl)buta-1',3'-diynyl]benzamido}-3-hydroxybutanoate

There total 6 articles about methyl (2S,3S)-2-{4'-[(4-aminophenyl)buta-1',3'-diynyl]benzamido}-3-hydroxybutanoate 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: 92.0%

4-[(4'-aminophenyl)buta-1,3-diyn-1-yl]benzoic acid (728878-27-1) + (L)-allo-threonine methyl ester hydrochloride (39994-75-7,60538-15-0,60538-18-3,62076-66-8,76419-75-5,79617-27-9,108724-12-5) → methyl (2S,3S)-2-{4'-[(4-aminophenyl)buta-1',3'-diynyl]benzamido}-3-hydroxybutanoate (1276668-07-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.bmc.2010.12.017

Reference yield: 92.0%

4-[(4'-aminophenyl)buta-1,3-diyn-1-yl]benzoic acid (728878-27-1) + (2S,3S)-methyl 2-amino-3-hydroxybutanoate hydrochloride → methyl (2S,3S)-2-{4'-[(4-aminophenyl)buta-1',3'-diynyl]benzamido}-3-hydroxybutanoate (1276668-07-5)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 19h; Inert atmosphere;

Reference yield:

methyl 4-iodobenzoate (619-44-3) → methyl (2S,3S)-2-{4'-[(4-aminophenyl)buta-1',3'-diynyl]benzamido}-3-hydroxybutanoate (1276668-07-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 22 h / 60 °C / Inert atmosphere

2.1: methanol; potassium carbonate / dichloromethane / 3 h / 20 °C

3.1: pyridine; copper diacetate / methanol / 48 h / 20 °C

4.1: water; sodium hydroxide / methanol / 1 h / Reflux

4.2: pH 2

5.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

With pyridine; methanol; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; water; copper diacetate; potassium carbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1.1: Sonogashira coupling / 3.1: Glaser coupling;

DOI:10.1016/j.bmc.2010.12.017

upstream raw materials:

4-[(4'-aminophenyl)buta-1,3-diyn-1-yl]benzoic acid

(L)-allo-threonine methyl ester hydrochloride

methyl 4-[(4'-aminophenyl)buta-1,3-diyn-1-yl]benzoate

methyl 4-iodobenzoate

Downstream raw materials:

4-[4-(4-aminophenyl)buta-1,3-diynyl]-N-{(1S,2S)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide