(S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide

Base Information

Chemical Name:(S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide
CAS No.:1132653-75-8
Molecular Formula:C₂₄H₂₅ClN₂O₄
Molecular Weight:440.927
Hs Code.:

Synonyms:(S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide

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Chemical Property of (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide

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Technology Process of (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide

There total 3 articles about (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide 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: 79.0%

: 104-86-9
4-chlorobenzylamine

: 851518-40-6
(S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid

: 1132653-75-8
(S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide

Guidance literature:: (S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)hex-5-enoic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 0.5h;

4-chlorobenzylamine; With dmap; In dichloromethane;
DOI:10.1016/j.bmcl.2009.09.089

Reference yield:

: 39716-58-0
pent-4-enoyl chloride

: 1132653-75-8
(S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: n-butyllithium / tetrahydrofuran; hexanes / 0.17 h / -78 °C

1.2: 1.5 h / -78 - 20 °C

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

2.2: 4 h / -78 - -48 °C

3.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C

With n-butyllithium; sodium hexamethyldisilazane; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; hexanes; dichloromethane;

Reference yield:

: 155399-10-3
(4R)-3-(4-pentenoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one

: 1132653-75-8
(S)-3-((R)-4-benzyl-2-oxooxazolidine-3-carbonyl)-N-(4-chlorobenzyl)hex-5-enamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

1.2: 4 h / -78 - -48 °C

2.1: trifluoroacetic acid / dichloromethane / 1 h / 20 °C

3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 °C

With sodium hexamethyldisilazane; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;