[R-(E)]-3-(1-Oxo-2-pentenyl)-4-phenyl-2-oxazolidinone

Base Information

• Chemical Name: [R-(E)]-3-(1-Oxo-2-pentenyl)-4-phenyl-2-oxazolidinone
• CAS No.: 188559-05-9
• Molecular Formula: C14H15 N O3
• Molecular Weight: 245.278
• Mol file: 188559-05-9.mol

Synonyms:2-Oxazolidinone,3-(1-oxo-2-pentenyl)-4-phenyl-, [R-(E)]-; 2-Oxazolidinone,3-[(2E)-1-oxo-2-pentenyl]-4-phenyl-, (4R)- (9CI)

Chemical Property of [R-(E)]-3-(1-Oxo-2-pentenyl)-4-phenyl-2-oxazolidinone

Chemical Property:

• PSA: 46.61000
• LogP: 2.61060
• Solubility.: Dichloromethane, Diethyl Ether, Ethyl Acetate

Purity/Quality:

99% ^*data from raw suppliers

[R-(E)]-3-(1-Oxo-2-pentenyl)-4-phenyl-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: [R-(E)]-3-(1-Oxo-2-pentenyl)-4-phenyl-2-oxazolidinone (cas# 188559-05-9) is a compound useful in organic synthesis.

Technology Process of [R-(E)]-3-(1-Oxo-2-pentenyl)-4-phenyl-2-oxazolidinone

There total 1 articles about [R-(E)]-3-(1-Oxo-2-pentenyl)-4-phenyl-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: 95.0%

(E)-pent-2-enoyl chloride (33698-85-0) + (4R)-phenyl-2-oxazolidinone (90319-52-1,7480-32-2) → (R)-N-[(E)-EtCHCHC(O)]-4-phenyl-1,3-oxazolidin-2-one (188559-05-9)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃;

DOI:10.1021/ja963434w

Reference yield: 96.0%

Ni(OC(O)CH2NC(C6H5)C6H4NC(O)CHCH2CH2CH2NCH2C6H5) + (R)-N-[(E)-EtCHCHC(O)]-4-phenyl-1,3-oxazolidin-2-one (188559-05-9) → Ni(OC(O)CH(CH(C2H5)CH2C(O)NC(O)OCH2CHC6H5)NC(C6H5)C6H4NC(O)CHCH2CH2CH2NCH2C6H5)

Guidance literature:

With catalyst: DBU; In N,N-dimethyl-formamide; N-(enoyl)-4-phenyl-1,3-oxazolidin-2-one (1.05-1.1 equiv.) added with stirring to suspn. of Ni complex in DMF; stirred at room temp. (22°C) for 10-15 min; DBU (15 mol%) added dropwise; 2 h; monitored by thin-layer chromy.; poured into icy 5% aq. acetic acid; stirred; filtered; ppt. washed with H2O; dried in vac.;

DOI:10.1021/ja0535561

Reference yield:

(R)-N-[(E)-EtCHCHC(O)]-4-phenyl-1,3-oxazolidin-2-one (188559-05-9) → tipranavir (174484-41-4,174484-81-2,174590-27-3)

Guidance literature:

Multi-step reaction with 7 steps

1: CuBr, DMS / tetrahydrofuran / 1 h / 0 °C

2: 1.) H₃O⁺, 2.) Na₂CO₃ / 2.) H₂O, CH₂Cl₂

5: 67 percent / t-BuOK / tetrahydrofuran / 0 °C

6: H₂ / Pd/C / methanol; ethyl acetate

7: 81 percent / pyridine / CH₂Cl₂

With pyridine; 2,3-dimercapto-succinic acid; oxonium; potassium tert-butylate; hydrogen; sodium carbonate; copper(I) bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate;

DOI:10.1021/ja963434w

upstream raw materials:

(E)-pent-2-enoyl chloride

(4R)-phenyl-2-oxazolidinone

Downstream raw materials:

tipranavir

<3α(R)>-3-<1-(3-aminophenyl)propyl>-5,6-dihydro-6,6-dipropyl-4-hydroxy-2H-pyran-2-one

(R)-3-[(R)-1-(3-Amino-phenyl)-propyl]-4-hydroxy-6-phenethyl-6-propyl-5,6-dihydro-pyran-2-one

3-[(R)-1-(3-Dibenzylamino-phenyl)-propyl]-4-hydroxy-6,6-dipropyl-5,6-dihydro-pyran-2-one

Refernces