(4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone

Base Information

• Chemical Name: (4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone
• CAS No.: 198649-20-6
• Molecular Formula: C₂₂H₃₃NO₃
• Molecular Weight: 359.509
• Mol file: 198649-20-6.mol

Synonyms:(4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone

Chemical Property of (4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone

There total 7 articles about (4S)-3-(dodecanoyl)-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: 97.0%

lauric acid (143-07-7) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone (198649-20-6)

Guidance literature:

lauric acid; With pivaloyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; Inert atmosphere;

(S)-4-Benzyl-2-oxazolidinone; With n-butyllithium; In tetrahydrofuran; Inert atmosphere;

DOI:10.1016/j.ejmech.2020.112408

Reference yield: 93.0%

n-dodecanoyl chloride (112-16-3) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone (198649-20-6)

Guidance literature:

(S)-4-Benzyl-2-oxazolidinone; With n-butyllithium; In tetrahydrofuran;

n-dodecanoyl chloride; In tetrahydrofuran;

DOI:10.1021/ja035085t

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (4S)-3-(dodecanoyl)-4-benzyl-2-oxazolidinone (198649-20-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 83 percent / BF₃*OEt₂; BH₃*SMe₂ / tetrahydrofuran

2.1: 69 percent / K₂CO₃

3.1: n-BuLi / tetrahydrofuran

3.2: 93 percent / tetrahydrofuran

With n-butyllithium; dimethylsulfide borane complex; boron trifluoride diethyl etherate; potassium carbonate; In tetrahydrofuran;

DOI:10.1021/ja035085t

upstream raw materials:

(S)-4-benzyl-2-oxazolidinone lithium salt

n-dodecanoyl chloride

(S)-4-Benzyl-2-oxazolidinone

L-phenylalanine

Downstream raw materials:

(4S)-4-benzyl-3-{(2S)-2-[(1R)-1-hydroxyoctyl]dodecanoyl}-2-oxazolidinone

(2R)-2-[(1S)-3-phenyl-1-(tetrahydropyran-2-yloxy)propyl]dodecanoic acid

(S)-4-Benzyl-3-{(S)-2-[(R)-3-phenyl-1-(tetrahydro-pyran-2-yloxy)-propyl]-dodecanoyl}-oxazolidin-2-one

(S)-4-Benzyl-3-{(S)-2-[(R)-1-(tetrahydro-pyran-2-yloxy)-octyl]-dodecanoyl}-oxazolidin-2-one

Refernces

• 1、 Aldrich, Courtney C.,Baran, Marzena,Boshoff, Helena I. M.,Fu, Peng,Grimes, Kimberly D.,Sibbald, Paul A.,Wilson, Daniel J.. "Development of small-molecule inhibitors of fatty acyl-AMP and fatty acyl-CoA ligases in Mycobacterium tuberculosis". . . Retrieved 2020/06/29.
• 2、 Hermann, Christoph,Giammasi, Chiara,Geyer, Armin,Maier, Martin E. "Syntheses of hapalosin analogs by solid-phase assembly of acyclic precursors". . p. 8999 - 9010. Retrieved 2007/10/03.