(4S)-4-benzyl-3-{[(1R,3R)-2,2-dimethyl-3-phenylcyclopropyl]carbonyl}-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4S)-4-benzyl-3-{[(1R,3R)-2,2-dimethyl-3-phenylcyclopropyl]carbonyl}-1,3-oxazolidin-2-one
• CAS No.: 1557242-99-5
• Molecular Formula: C₂₂H₂₃NO₃
• Molecular Weight: 349.43
• Mol file: 1557242-99-5.mol

Synonyms:(4S)-4-benzyl-3-{[(1R,3R)-2,2-dimethyl-3-phenylcyclopropyl]carbonyl}-1,3-oxazolidin-2-one

Chemical Property of (4S)-4-benzyl-3-{[(1R,3R)-2,2-dimethyl-3-phenylcyclopropyl]carbonyl}-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-benzyl-3-{[(1R,3R)-2,2-dimethyl-3-phenylcyclopropyl]carbonyl}-1,3-oxazolidin-2-one

There total 3 articles about (4S)-4-benzyl-3-{[(1R,3R)-2,2-dimethyl-3-phenylcyclopropyl]carbonyl}-1,3-oxazolidin-2-one 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:

(+/-)-2,2-dimethyl-3t-phenyl-cyclopropane-r-carbonyl chloride (4489-17-2,54864-31-2) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (4S)-4-benzyl-3-{[(1R,3R)-2,2-dimethyl-3-phenylcyclopropyl]carbonyl}-1,3-oxazolidin-2-one (1557242-99-5) + (4S)-4-benzyl-3-{[(1S,3S)-2,2-dimethyl-3-phenylcyclopropyl]carbonyl}-1,3-oxazolidin-2-one (1557243-03-4)

Guidance literature:

(S)-4-Benzyl-2-oxazolidinone; With n-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.5h; Inert atmosphere;

(+/-)-2,2-dimethyl-3t-phenyl-cyclopropane-r-carbonyl chloride; In tetrahydrofuran; cyclohexane; at -78 - 20 ℃; Inert atmosphere;

DOI:10.1021/acsmedchemlett.9b00001

Reference yield:

(±)-trans-2,2-dimethyl-3-phenylcyclopropanecarboxylic acid (50672-13-4,99647-69-5) → (4S)-4-benzyl-3-{[(1R,3R)-2,2-dimethyl-3-phenylcyclopropyl]carbonyl}-1,3-oxazolidin-2-one (1557242-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1.75 h / 0 - 20 °C / Inert atmosphere

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

2.2: -78 - 20 °C / Inert atmosphere

With n-butyllithium; oxalyl dichloride; N,N-dimethyl-formamide; In tetrahydrofuran; dichloromethane; cyclohexane;

DOI:10.1021/acsmedchemlett.9b00001

Reference yield:

→ (4S)-4-benzyl-3-{[(1R,3R)-2,2-dimethyl-3-phenylcyclopropyl]carbonyl}-1,3-oxazolidin-2-one (1557242-99-5) + (4S)-4-benzyl-3-{[(1S,3S)-2,2-dimethyl-3-phenylcyclopropyl]carbonyl}-1,3-oxazolidin-2-one (1557243-03-4)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.5h; Inert atmosphere;

In tetrahydrofuran; cyclohexane; at -78 - 20 ℃; Overall yield = 71 %; Inert atmosphere;

upstream raw materials:

(±)-trans-2,2-dimethyl-3-phenylcyclopropanecarboxylic acid

(+/-)-2,2-dimethyl-3t-phenyl-cyclopropane-r-carbonyl chloride

(S)-4-Benzyl-2-oxazolidinone

Downstream raw materials:

4-((1R,3R)-3-(((5-chloro-2-methoxyphenyl)amino)methyl)-2,2-dimethylcyclopropyl)-benzenesulfonamide

(1R,3R)-N-(5-fluoro-2-methylphenyl)-2,2-dimethyl-3-(4-sulfamoylphenyl)cyclopropanecarboxamide

(1R,3R)-N-(4,5-difluoro-2-methylphenyl)-2,2-dimethyl-3-(4-sulfamoylphenyl)cyclopropanecarboxamide

(1R,3R)-N-(5-fluoro-2-methylphenyl)-2,2-dimethyl-3-phenylcyclopropanecarboxamide