(4R)-3-[(2S)-1-Oxo-2-(2-propenyl)octyl]-4-benzyl-2-oxazolidinone

Base Information

• Chemical Name: (4R)-3-[(2S)-1-Oxo-2-(2-propenyl)octyl]-4-benzyl-2-oxazolidinone
• CAS No.: 548783-48-8
• Molecular Formula: C₂₁H₂₉NO₃
• Molecular Weight: 343.466
• Mol file: 548783-48-8.mol

Synonyms:(4R)-3-[(2S)-1-Oxo-2-(2-propenyl)octyl]-4-benzyl-2-oxazolidinone;(4R)-3-[(2S)-1-Oxo-2-(2-propenyl)octyl]-4-(phenylMethyl)-2-oxazolidinone

Chemical Property of (4R)-3-[(2S)-1-Oxo-2-(2-propenyl)octyl]-4-benzyl-2-oxazolidinone

Chemical Property:

• PSA: 46.61000
• LogP: 4.67710
• Solubility.: Dichloromethane, Ether, Ethyl Acetate, Tetrahydrofuran

Purity/Quality:

97% ^*data from raw suppliers

(4R)-3-[(2S)-1-Oxo-2-(2-propenyl)octyl]-4-benzyl-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Arundic Acid intermediate.

Technology Process of (4R)-3-[(2S)-1-Oxo-2-(2-propenyl)octyl]-4-benzyl-2-oxazolidinone

There total 6 articles about (4R)-3-[(2S)-1-Oxo-2-(2-propenyl)octyl]-4-benzyl-2-oxazolidinone 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: 64.0%

allyl bromide (106-95-6) + (4R)-3-(octanoyl)-4-benzyl-2-oxazolidinone (162737-63-5) → (R)-3-((S)-2-allyloctanoyl)-4-benzyloxazolidin-2-one (548783-48-8)

Guidance literature:

(4R)-3-(octanoyl)-4-benzyl-2-oxazolidinone; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

allyl bromide; In tetrahydrofuran; at -78 - 0 ℃; for 1.75h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.6b00124

Reference yield: 60.0%

allyl bromide (106-95-6) + (4S)-4-benzyl-3-octanoyl-1,3-oxazolidin-2-one (152899-13-3) → (S)-3-((R)-2-allyloctanoyl)-4-benzyloxazolidin-2-one (548783-48-8)

Guidance literature:

(4S)-4-benzyl-3-octanoyl-1,3-oxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; at -78 ℃; for 1h; Inert atmosphere;

allyl bromide; In tetrahydrofuran; at -78 - 0 ℃; for 1.75h; Inert atmosphere;

DOI:10.1021/acsmedchemlett.6b00124

Reference yield:

n-octanoic acid chloride (111-64-8) → (S)-3-((R)-2-allyloctanoyl)-4-benzyloxazolidin-2-one (548783-48-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

1.2: 1 h / -78 - 20 °C / Inert atmosphere

2.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

2.2: 1.75 h / -78 - 0 °C / Inert atmosphere

With n-butyllithium; sodium hexamethyldisilazane; In tetrahydrofuran;

DOI:10.1021/acsmedchemlett.6b00124

upstream raw materials:

(S)-4-Benzyl-2-oxazolidinone

n-octanoic acid chloride

allyl bromide

(4S)-4-benzyl-3-octanoyl-1,3-oxazolidin-2-one