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

Base Information

Chemical Name:4-[4-(4-aminophenyl)buta-1,3-diynyl]-N-{(1S,2S)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide
CAS No.:728877-74-5
Molecular Formula:C₂₁H₁₉N₃O₄
Molecular Weight:377.4
Hs Code.:

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

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

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

There total 6 articles about 4-[4-(4-aminophenyl)buta-1,3-diynyl]-N-{(1S,2S)-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: 70.0%

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

: 728877-74-5
4-[4-(4-aminophenyl)buta-1,3-diynyl]-N-{(1S,2S)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide

Guidance literature:: With hydroxylamine hydrochloride; sodium methylate; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 16h; Inert atmosphere;
DOI:10.1016/j.bmc.2010.12.017

Reference yield:

: 3034-86-4
4-ethynylbenzoic acid methyl ester

: 728877-74-5
4-[4-(4-aminophenyl)buta-1,3-diynyl]-N-{(1S,2S)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide

Guidance literature:: Multi-step reaction with 4 steps

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

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

2.2: pH 2

3.1: 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

4.1: hydroxylamine hydrochloride; sodium methylate / tetrahydrofuran; methanol / 16 h / 0 - 20 °C / Inert atmosphere

With pyridine; hydroxylamine hydrochloride; water; sodium methylate; copper diacetate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; 1.1: Glaser coupling;
DOI:10.1016/j.bmc.2010.12.017

Reference yield:

: 75867-41-3
4-trimethylsilanylethynyl-benzoic acid methyl ester

: 728877-74-5
4-[4-(4-aminophenyl)buta-1,3-diynyl]-N-{(1S,2S)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide

Guidance literature:: Multi-step reaction with 5 steps

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

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

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

3.2: pH 2

4.1: 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

5.1: hydroxylamine hydrochloride; sodium methylate / tetrahydrofuran; methanol / 16 h / 0 - 20 °C / Inert atmosphere

With pyridine; methanol; hydroxylamine hydrochloride; water; sodium methylate; 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; 2.1: Glaser coupling;
DOI:10.1016/j.bmc.2010.12.017