2-Oxazolidinone, 3-[(2E)-1-oxo-2-butenyl]-4-phenyl-, (4R)-

Base Information

• Chemical Name: 2-Oxazolidinone, 3-[(2E)-1-oxo-2-butenyl]-4-phenyl-, (4R)-
• CAS No.: 148766-15-8
• Molecular Formula: C13H13NO3
• Molecular Weight: 231.251
• Mol file: 148766-15-8.mol

Synonyms:

Chemical Property of 2-Oxazolidinone, 3-[(2E)-1-oxo-2-butenyl]-4-phenyl-, (4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Oxazolidinone, 3-[(2E)-1-oxo-2-butenyl]-4-phenyl-, (4R)-

There total 14 articles about 2-Oxazolidinone, 3-[(2E)-1-oxo-2-butenyl]-4-phenyl-, (4R)- 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: 94.0%

trans-chrotonyl chloride (625-35-4,3488-22-0,10487-71-5) + (S)-4-phenyl-2-oxazolidinone (99395-88-7,7480-32-2) → (4S)-3-((2E)-2-butenoyl)-4-phenyl-1,3-oxazolidin-2-one (111292-75-2,148766-15-8,112530-01-5)

Guidance literature:

(S)-4-phenyl-2-oxazolidinone; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.25h;

trans-chrotonyl chloride; In tetrahydrofuran; at -78 - 0 ℃; for 0.75h;

DOI:10.1021/acs.joc.7b02104

Reference yield: 94.0%

(E)-but-2-enoic acid (107-93-7) + (4R)-4-phenyl-1,3-oxazolidin-2-one lithium amide → (R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one (148766-15-8)

Guidance literature:

(E)-but-2-enoic acid; With pivaloyl chloride; triethylamine; In tetrahydrofuran; at -78 - 0 ℃; for 1h; Inert atmosphere;

(4R)-4-phenyl-1,3-oxazolidin-2-one lithium amide; In tetrahydrofuran; hexane; at -78 - 23 ℃; for 16h; Inert atmosphere;

DOI:10.1021/np500925y

Reference yield: 91.0%

crotonic anhydride (623-68-7) + (S)-4-phenyl-2-oxazolidinone (99395-88-7,7480-32-2) → (4S)-3-((2E)-2-butenoyl)-4-phenyl-1,3-oxazolidin-2-one (111292-75-2,148766-15-8,112530-01-5)

Guidance literature:

(S)-4-phenyl-2-oxazolidinone; With triethylamine; lithium chloride; In tetrahydrofuran; at 23 ℃; for 0.333333h; Inert atmosphere; Large scale reaction;

crotonic anhydride; In tetrahydrofuran; at 15 - 23 ℃; for 1.5h; Inert atmosphere; Large scale reaction;

DOI:10.1016/j.tet.2009.06.022

upstream raw materials:

trans-chrotonyl chloride

(S)-4-phenyl-2-oxazolidinone

(S)-2-phenylglycine

(2S)-2-phenylglycinol

Downstream raw materials:

(4S)-N-[(3S)-phenylbutanoyl]-4-phenyl-1,3-oxazolidin-2-one

(4R)-4-phenyl-3-<(3R)-3-phenylbutyryl>oxazolidin-2-one

Refernces

• 1、 Vachal, Petr,Duffy, Joseph L.,Campeau, Louis-Charles,Amin, Rupesh P.,Mitra, Kaushik,Murphy, Beth Ann,Shao, Pengcheng P.,Sinclair, Peter J.,Ye, Feng,Katipally, Revathi,Lu, Zhijian,Ondeyka, Debra,Chen, Yi-Heng,Zhao, Kake,Sun, Wanying,Tyagarajan, Sriram,Bao, Jianming,Wang, Sheng-Ping,Cote, Josee,Lipardi, Concetta,Metzger, Daniel,Leung, Dennis,Hartmann, Georgy,Wollenberg, Gordon K.,Liu, Jian,Tan, Lushi,Xu, Yingju,Chen, Qinghao,Liu, Guiquan,Blaustein, Robert O.,Johns, Douglas G.. "Invention of MK-8262, a Cholesteryl Ester Transfer Protein (CETP) Inhibitor Backup to Anacetrapib with Best-in-Class Properties ()". supporting information. p. 13215 - 13258. Retrieved 2021/09/02.
• 2、 -. "Intermediate for preparing halichondrin compound and preparation method thereof". Paragraph 0132-0133; 0136-0138. . Retrieved 2020/07/07.