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

Base Information

• Chemical Name: 4-[4-(2-aminophenyl)buta-1,3-diynyl]-N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide
• CAS No.: 728875-33-0
• Molecular Formula: C₂₁H₁₉N₃O₄
• Molecular Weight: 377.4

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

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

Chemical Property:

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

There total 3 articles about 4-[4-(2-aminophenyl)buta-1,3-diynyl]-N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide 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: 74.0%

methyl (2S,3R)-2-{4'-[(2''-aminophenyl)buta-1',3'-diynyl]benzamido}-3-hydroxy-butanoate (1276668-06-4) → 4-[4-(2-aminophenyl)buta-1,3-diynyl]-N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide (728875-33-0)

Guidance literature:

With hydroxylamine hydrochloride; sodium methylate; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.bmc.2010.12.017

Reference yield: 74.0%

→ 4-[4-(2-aminophenyl)buta-1,3-diynyl]-N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide (728875-33-0)

Guidance literature:

Reference yield:

2-ethynylaniline (52670-38-9) + (2S,3R)-2-(4-ethynylbenzoylamino)-3-hydroxybutanoic acid methyl ester (728878-24-8) → 4-[4-(2-aminophenyl)buta-1,3-diynyl]-N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide (728875-33-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; copper diacetate / methanol / 80 h / 20 °C

2: hydroxylamine hydrochloride; sodium methylate / tetrahydrofuran; methanol / 18 h / 0 - 20 °C / Inert atmosphere

With pyridine; hydroxylamine hydrochloride; sodium methylate; copper diacetate; In tetrahydrofuran; methanol; 1: Glaser coupling;

DOI:10.1016/j.bmc.2010.12.017

upstream raw materials:

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

2-ethynylaniline

(2S,3R)-2-(4-ethynylbenzoylamino)-3-hydroxybutanoic acid methyl ester

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