2-{[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]oxy}acetic acid

Base Information

• Chemical Name: 2-{[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]oxy}acetic acid
• CAS No.: 1061605-21-7
• Molecular Formula: C₁₅H₁₂N₂O₇
• Molecular Weight: 332.269
• Hs Code.: 2933998090
• Mol file: 1061605-21-7.mol

Synonyms:

Chemical Property of 2-{[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]oxy}acetic acid

Chemical Property:

• Boiling Point: 660.5±55.0 °C(Predicted)
• Density: 1.606±0.06 g/cm3(Predicted)

Purity/Quality:

99% ^*data from raw suppliers

TCE35031 ≥98%(HPLC) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Description: Thalidomide-Acid is a linker of Thalidomide which is commonly used as a precursor to PROTAC that hijacks cereblon as the E3 ubiquitin ligase component.
• Uses: Thalidomide-4-hydroxyacetate is a proteolysis targeting chimeras which allows for the optical control of protein degradation.

Technology Process of 2-{[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]oxy}acetic acid

There total 19 articles about 2-{[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]oxy}acetic acid 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: 100.0%

tert-butyl 2-{[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]oxy}acetate → 2-{[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]oxy}acetic acid (1061605-21-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

Reference yield: 100.0%

benzyl 2-((2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindolin-4-yl)oxy)acetate → 2-{[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]oxy}acetic acid (1061605-21-7)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; In dichloromethane; ethyl acetate; for 3h; under 760.051 Torr;

DOI:10.1016/j.bmcl.2016.09.048

Reference yield: 90.0%

C20H20N2O9 → 2-{[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]oxy}acetic acid (1061605-21-7)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1021/acs.jmedchem.1c01069

upstream raw materials:

4-Hydroxythalidomide

3-hydroxyphthalic anhydride

3-nitrophthalic acid anhydride

3-aminophthalic anhydride

Downstream raw materials:

N-(2-[2-[2-(2-aminoethoxy)ethoxy]ethoxy]ethyl)-2-[[2-(2,6-dioxopiperidin-3-yl)-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl]oxy]acetamide

Refernces

• 1、 Cao, Chaoguo,Yang, Jie,Chen, Yong,Zhou, Peiting,Wang, Yingwei,Du, Wu,Zhao, Lifeng,Chen, Yuanwei. "Discovery of SK-575 as a Highly Potent and Efficacious Proteolysis-Targeting Chimera Degrader of PARP1 for Treating Cancers". . p. 11012 - 11033. Retrieved 2020.
• 2、 Xue, Gang,Wang, Kun,Zhou, Danli,Zhong, Hanbing,Pan, Zhengying. "Light-Induced Protein Degradation with Photocaged PROTACs". . p. 18370 - 18374. Retrieved 2019.
• 3、 Chessum, Nicola E. A.,Sharp, Swee Y.,Caldwell, John J.,Pasqua, A. Elisa,Wilding, Birgit,Colombano, Giampiero,Collins, Ian,Ozer, Bugra,Richards, Meirion,Rowlands, Martin,Stubbs, Mark,Burke, Rosemary,McAndrew, P. Craig,Clarke, Paul A.,Workman, Paul,Cheeseman, Matthew D.,Jones, Keith. "Demonstrating In-Cell Target Engagement Using a Pirin Protein Degradation Probe (CCT367766)". . p. 918 - 933. Retrieved 2018.
• 4、 Bae, Munhyung,Blacklow, Stephen C.,Cao, Ruili,Cuny, Gregory D.,Donovan, Katherine A.,Fischer, Eric S.,Henke, Matthew T.,Lumpkin, Ryan J.,Ray, Soumya S.,Rogers, Julia M.,Seegar, Tom C. M.,Vemulapalli, Vidyasiri. "Targeted Degradation of the Oncogenic Phosphatase SHP2". . p. 2593 - 2609. Retrieved 2021.
• 5、 Zhou, Fei,Chen, Luyu,Cao, Chaoguo,Yu, Jiang,Luo, Xiaojiao,Zhou, Peiting,Zhao, Lifeng,Du, Wu,Cheng, Jijun,Xie, Yongmei,Chen, Yuanwei. "Development of selective mono or dual PROTAC degrader probe of CDK isoforms". . . Retrieved 2020.
• 6、 Niu, Tian,Li, Kailin,Jiang, Li,Zhou, Zhesheng,Hong, Ju,Chen, Xuankun,Dong, Xiaowu,He, Qiaojun,Cao, Ji,Yang, Bo,Zhu, Cheng-Liang. "Noncovalent CDK12/13 dual inhibitors-based PROTACs degrade CDK12-Cyclin K complex and induce synthetic lethality with PARP inhibitor". supporting information. . Retrieved 2021/12/09.
• 7、 -. "TARGETED DEGRADERS OF ABERRANT TAU BASED ON THE PET TRACER PBB3". Paragraph 00140; 00143. . Retrieved 2021/09/26.