(4S)-4-Benzyl-5,5-dimethyl-3-(6-heptenoyl)-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4S)-4-Benzyl-5,5-dimethyl-3-(6-heptenoyl)-1,3-oxazolidin-2-one
• CAS No.: 250280-59-2
• Molecular Formula: C₁₉H₂₅NO₃
• Molecular Weight: 315.412
• Mol file: 250280-59-2.mol

Synonyms:(4S)-4-Benzyl-5,5-dimethyl-3-(6-heptenoyl)-1,3-oxazolidin-2-one

Chemical Property of (4S)-4-Benzyl-5,5-dimethyl-3-(6-heptenoyl)-1,3-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-Benzyl-5,5-dimethyl-3-(6-heptenoyl)-1,3-oxazolidin-2-one

There total 2 articles about (4S)-4-Benzyl-5,5-dimethyl-3-(6-heptenoyl)-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: 65.0%

6-heptenoyl chloride (21430-12-6) + (S)-4-benzyl-5,5-dimethyloxazolidin-2-one (168297-85-6,352438-06-3) → (4S)-4-Benzyl-5,5-dimethyl-3-(6-heptenoyl)-1,3-oxazolidin-2-one (250280-59-2)

Guidance literature:

(S)-4-benzyl-5,5-dimethyloxazolidin-2-one; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

6-heptenoyl chloride; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2483::AID-CHEM2483>3.0.CO;2-N

Reference yield:

hept-6-enoic acid (1119-60-4) → (4S)-4-Benzyl-5,5-dimethyl-3-(6-heptenoyl)-1,3-oxazolidin-2-one (250280-59-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: (COCl)2 / CH₂Cl₂ / 3.25 h

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: 65 percent / tetrahydrofuran; hexane / -78 - 20 °C

With n-butyllithium; oxalyl dichloride; In tetrahydrofuran; hexane; dichloromethane; 1.1: Substitution / 2.1: Metallation / 2.2: Acylation;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2483::AID-CHEM2483>3.0.CO;2-N

Reference yield: 85.0%

(4S)-4-Benzyl-5,5-dimethyl-3-(6-heptenoyl)-1,3-oxazolidin-2-one (250280-59-2) + methyl iodide (74-88-4) → (4S)-4-Benzyl-5,5-dimethyl-3-[(2S)-2-methyl-6-heptenoyl]-1,3-oxazolidin-2-one (250280-60-5)

Guidance literature:

(4S)-4-Benzyl-5,5-dimethyl-3-(6-heptenoyl)-1,3-oxazolidin-2-one; With sodium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

methyl iodide; With triphenylphosphine; In tetrahydrofuran; diethyl ether; at -78 ℃; for 0.5h;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2483::AID-CHEM2483>3.0.CO;2-N

upstream raw materials:

6-heptenoyl chloride

(S)-4-benzyl-5,5-dimethyloxazolidin-2-one

hept-6-enoic acid

Downstream raw materials:

(4S)-4-Benzyl-5,5-dimethyl-3-[(2S)-2-methyl-6-heptenoyl]-1,3-oxazolidin-2-one