(4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one
• CAS No.: 128891-66-7
• Molecular Formula: C₁₉H₁₇NO₃
• Molecular Weight: 307.349
• Mol file: 128891-66-7.mol

Synonyms:(4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one

Chemical Property of (4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-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-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one

There total 5 articles about (4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-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: 98.0%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) + Cinnamoyl chloride (102-92-1,17082-09-6) → (4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one (128891-66-7)

Guidance literature:

With triethylamine; lithium chloride; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1002/1522-2675(200211)85:11<3616::AID-HLCA3616>3.0.CO;2-O

Reference yield: 96.0%

(E)-3-phenylacrylic acid (140-10-3) + (S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one (128891-66-7)

Guidance literature:

(E)-3-phenylacrylic acid; With pivaloyl chloride; triethylamine; In tetrahydrofuran; at -40 ℃; for 2h; Inert atmosphere;

(S)-4-Benzyl-2-oxazolidinone; With lithium chloride; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;

DOI:10.1002/ejoc.201800262

Reference yield: 54.0%

(S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one (136159-65-4,96930-27-7) → (4S)-4-benzyl-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one (128891-66-7)

Guidance literature:

(S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one; With n-butyllithium; N-cyclohexyl-2,6-diisopropylaniline; In tetrahydrofuran; hexane; at -40 ℃; for 0.5h; Cooling with ice; Inert atmosphere;

With zinc(II) chloride; In tetrahydrofuran; hexane; for 0.5h; Cooling with ice; Inert atmosphere;

With bis(η3-allyl-μ-chloropalladium(II)); Allyl acetate; In tetrahydrofuran; hexane; for 10h; Cooling with ice; Heating; Inert atmosphere;

DOI:10.1021/jacs.5b12924

upstream raw materials:

(S)-4-Benzyl-2-oxazolidinone

Cinnamoyl chloride

(E)-3-phenylacrylic acid

(S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one

Downstream raw materials:

(4S)-3-((3S)-3-phenylhex-5-enoyl)-4-benzyl-1,3-oxazolidin-2-one

(4S,3'R)-3-(3'-amino-3'-phenylpropanoyl)-4-benzyloxazolidin-2-one