1-[(4S)-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl]-ethanone

Base Information

• Chemical Name: 1-[(4S)-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl]-ethanone
• CAS No.: 445040-77-7
• Molecular Formula: C₂₀H₂₁NO₂S
• Molecular Weight: 339.458
• Mol file: 445040-77-7.mol

Synonyms:1-[(4S)-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl]-ethanone

Chemical Property of 1-[(4S)-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl]-ethanone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(4S)-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl]-ethanone

There total 2 articles about 1-[(4S)-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl]-ethanone 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: 96.0%

(4S)-isopropyl-5,5-diphenyl-oxazolidine-2-thione (191274-53-0) + acetyl chloride (75-36-5) → 1-[(4S)-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl]-ethanone (445040-77-7)

Guidance literature:

(4S)-isopropyl-5,5-diphenyl-oxazolidine-2-thione; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.25h;

acetyl chloride; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Further stages.;

DOI:10.1021/ol026108w

Reference yield:

(L)-valine methyl ester hydrochloride (5619-05-6,6306-52-1,7146-15-8) → 1-[(4S)-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl]-ethanone (445040-77-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: diethyl ether / 12 h / 20 °C

1.2: 42 percent / Et₃N / tetrahydrofuran / 14 h / Heating

2.1: sodium hydride / tetrahydrofuran / 0.25 h / 0 °C

2.2: 96 percent / tetrahydrofuran / 2 h / 0 - 20 °C

With sodium hydride; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ol026108w

Reference yield: 90.0%

propionaldehyde (123-38-6) + 1-[(4S)-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl]-ethanone (445040-77-7) → 3-hydroxy-1-[(4S)-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl]-pentan-1-one

Guidance literature:

1-[(4S)-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl]-ethanone; With 1-methyl-pyrrolidin-2-one; titanium tetrachloride; (-)-sparteine; In dichloromethane; at 0 ℃; for 0.333333h;

propionaldehyde; In dichloromethane; at -78 ℃; for 1h; Further stages.;

DOI:10.1021/ol026108w

upstream raw materials:

(4S)-isopropyl-5,5-diphenyl-oxazolidine-2-thione

acetyl chloride

(L)-valine methyl ester hydrochloride

Downstream raw materials:

(3S,5S)-5-[(R)-1-(1,1-Dimethyl-2-triisopropylsilanyloxy-ethyl)-allyloxy]-3-hydroxy-1-((S)-4-isopropyl-5,5-diphenyl-2-thioxo-oxazolidin-3-yl)-oct-7-en-1-one