(2S,3R)-2-[4-(4-formylphenylethynyl)benzoylamino]-3-hydroxybutyric acid methyl ester

Base Information

Chemical Name:(2S,3R)-2-[4-(4-formylphenylethynyl)benzoylamino]-3-hydroxybutyric acid methyl ester
CAS No.:728878-11-3
Molecular Formula:C₂₁H₁₉NO₅
Molecular Weight:365.386
Hs Code.:

Synonyms:(2S,3R)-2-[4-(4-formylphenylethynyl)benzoylamino]-3-hydroxybutyric acid methyl ester

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Chemical Property of (2S,3R)-2-[4-(4-formylphenylethynyl)benzoylamino]-3-hydroxybutyric acid methyl ester

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Technology Process of (2S,3R)-2-[4-(4-formylphenylethynyl)benzoylamino]-3-hydroxybutyric acid methyl ester

There total 4 articles about (2S,3R)-2-[4-(4-formylphenylethynyl)benzoylamino]-3-hydroxybutyric acid methyl 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: 80.0%

: 728878-24-8
(2S,3R)-2-(4-ethynylbenzoylamino)-3-hydroxybutanoic acid methyl ester

: 15164-44-0
p-(iodophenyl)carboxaldehyde

: 728878-11-3
(2S,3R)-2-[4-(4-formylphenylethynyl)benzoylamino]-3-hydroxybutyric acid methyl ester

Guidance literature:: With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; triethylamine; In tetrahydrofuran; for 40h; Inert atmosphere;

Reference yield:

: 619-44-3
methyl 4-iodobenzoate

: 728878-11-3
(2S,3R)-2-[4-(4-formylphenylethynyl)benzoylamino]-3-hydroxybutyric acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 0.5 h / 20 °C / Inert atmosphere

1.2: 18 h / 20 - 100 °C / Inert atmosphere; Sealed tube

2.1: sodium hydroxide / ethanol / 18 h / 20 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C

3.2: 18 h / 20 °C

4.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; In tetrahydrofuran; ethanol; acetonitrile;
DOI:10.1016/j.bmcl.2013.02.055

Reference yield:

: 144693-65-2
4-ethynylbenzoic acid sodium salt

: 728878-11-3
(2S,3R)-2-[4-(4-formylphenylethynyl)benzoylamino]-3-hydroxybutyric acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C

1.2: 18 h / 20 °C

2.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran;
DOI:10.1016/j.bmcl.2013.02.055