(R)-6-azido-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hexanoic acid tert-butyl ester

Base Information

Chemical Name:(R)-6-azido-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hexanoic acid tert-butyl ester
CAS No.:1424402-09-4
Molecular Formula:C₂₁H₂₈N₄O₅
Molecular Weight:416.477
Hs Code.:

Synonyms:(R)-6-azido-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hexanoic acid tert-butyl ester

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Chemical Property of (R)-6-azido-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hexanoic acid tert-butyl ester

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Technology Process of (R)-6-azido-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hexanoic acid tert-butyl ester

There total 4 articles about (R)-6-azido-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hexanoic acid tert-butyl 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: 87.0%

: 868248-75-3
(4S)-3-(5-azido-1-oxovaleryl)-4-benzyl-2-oxazolidinone

: 5292-43-3
bromoacetic acid tert-butyl ester

: 1424402-09-4
(R)-6-azido-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hexanoic acid tert-butyl ester

Guidance literature:: (4S)-3-(5-azido-1-oxovaleryl)-4-benzyl-2-oxazolidinone; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 0.5h; Inert atmosphere;

bromoacetic acid tert-butyl ester; With sodium iodide; In tetrahydrofuran; at 20 ℃; for 0.5h; stereoselective reaction; Inert atmosphere;
DOI:10.1021/jm301346z

Reference yield:

: 156699-37-5
(S)-4-benzyl-3-(5-bromopentanoyl)oxazolidine-2-one

: 1424402-09-4
(R)-6-azido-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium azide / water; acetone / 72 h / 20 °C / Reflux; Inert atmosphere

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

2.2: 0.5 h / 20 °C / Inert atmosphere

With sodium azide; sodium hexamethyldisilazane; In tetrahydrofuran; water; acetone;
DOI:10.1021/jm301346z

Reference yield:

: 2067-33-6
5-bromopentanoic acid

: 1424402-09-4
(R)-6-azido-3-((S)-4-benzyl-2-oxooxazolidine-3-carbonyl)hexanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: thionyl chloride / dichloromethane; N,N-dimethyl-formamide / 3 °C / Reflux; Inert atmosphere

2.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: sodium azide / water; acetone / 72 h / 20 °C / Reflux; Inert atmosphere

4.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

4.2: 0.5 h / 20 °C / Inert atmosphere

With n-butyllithium; thionyl chloride; sodium azide; sodium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/jm301346z