N,N-Bis(2-(2,6-dioxo-4-morpholinyl)ethyl]glycine

Base Information

• Chemical Name: N,N-Bis(2-(2,6-dioxo-4-morpholinyl)ethyl]glycine
• CAS No.: 23911-26-4
• Molecular Formula: C14H19N3O8
• Molecular Weight: 375.335
• Hs Code.: 29224999
• Mol file: 23911-26-4.mol

Synonyms:diethylenetriamine pentaacetic acid dianhydride;dtpaa-gd

Chemical Property of N,N-Bis(2-(2,6-dioxo-4-morpholinyl)ethyl]glycine

Chemical Property:

• Appearance/Colour: white or cream white solid
• Vapor Pressure: 6.53E-19mmHg at 25°C
• Melting Point: 182-184 °C(lit.)
• Refractive Index: 1.558
• Boiling Point: 656.2 °C at 760 mmHg
• PKA: 2.19±0.10(Predicted)
• Flash Point: 350.6 °C
• PSA: 133.76000
• Density: 1.46 g/cm³
• LogP: -2.98040
• Storage Temp.: −20°C
• Sensitive.: Moisture Sensitive
• Water Solubility.: Hydrolyzes in water.
• XLogP3: -2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 7
• Exact Mass: 357.11721457
• Heavy Atom Count: 25
• Complexity: 499

Purity/Quality:

99.9% ^*data from raw suppliers

NSC379317 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(=O)OC(=O)CN1CC[NH+](CCN2CC(=O)OC(=O)C2)CC(=O)[O-]
• Uses: NSC 379317 or DTPAA is a useful synthetic intermediate in producing DPTA, in which it is used to synthesize the GO-DEN(Gd-DTPA)-mAb, a contrast reagent for prostate tumor MRI imaging. GO-DEN(Gd-DTPA)-mAb can be coupled with DOX to produce GO-DEN(Gd-DTPA)-mAb/DOX, creating an effective delivery of anti cancer drugs to the prostate cancer cells, PC-3, in mice.

Technology Process of N,N-Bis(2-(2,6-dioxo-4-morpholinyl)ethyl]glycine

There total 5 articles about N,N-Bis(2-(2,6-dioxo-4-morpholinyl)ethyl]glycine 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: 99.0%

diethylenetriaminopentaacetic acid (67-43-6,84932-15-0) → diethylenetriaminepentaacetic dianhydride (23911-26-4)

Guidance literature:

With pyridine; acetic anhydride; at 80 ℃; for 24h;

DOI:10.1039/c7ob01068k

Reference yield: 83.0%

diethylenetriaminopentaacetic acid (67-43-6,84932-15-0) + acetic anhydride (108-24-7) → diethylenetriaminepentaacetic dianhydride (23911-26-4)

Guidance literature:

With pyridine; at 65 ℃; for 24h;

DOI:10.1016/j.saa.2017.02.048

Reference yield:

→ diethylenetriaminepentaacetic dianhydride (23911-26-4)

Guidance literature:

DOI:10.1002/jps.2600640433

upstream raw materials:

diethylenetriaminopentaacetic acid

acetic anhydride

Downstream raw materials:

3,9-bis[2-(benzyloxy)-2-oxoethyl]-6-(carboxymethyl)-3,6,9-triazaundecanedioic acid

N-(4-carboxy-3-hydroxyphenylcarbamoylmethyl)-N,N',N'',N''-diethylenetriaminetetraacetic acid

(HOOCCH₂)(4-HOOC-3-HO-C₆H₃NHCOCH₂)NCH₂CH₂N(CH₂COOH)CH₂CH₂N(CH₂COOH)(CH₂CONHC₆H₃-3-OH-4-COOH)

Refernces

• 1、 Liu, Wenfang,Wang, Bingqiang,Jia, Haishuang,Wang, Jun,Song, Youtao. "A dual-excitation fluorescent probe EuIII-dtpa-bis(HBT) for hydrazine detection in aqueous solutions and living cells". . p. 16478 - 16489. Retrieved 2019.
• 2、 Zhang, Xue-Li,Zhang, Ding-Wa,Zhang, Hui-Jiao,He, Shi-Ni,Chen, Yao-Ting. "Synthesis soluble non-ion transition metal manganese(II), cobalt(II), nickel(II) complexes of diethylenetriamine-N,N′,N″-tri(acetyl-p-hydroxybenzoyl hydrazine)- N,N″- bisacetic acid as potential contrast enhancement agent". . p. 346 - 349. Retrieved 2015.
• 3、 Yu, Zhiyue,Jia, Haishuang,Li, Na,Liu, Wenfang,Wang, Jun,Song, Youtao. "Design and synthesis of a novel fluorescent probe, euiii-dtpa-bis(Adenine), and application for the detection of orotic acid in urine". . p. 763 - 771. Retrieved 2019.
• 4、 Brunet, Ernesto,Juanes, Olga,Sedano, Rosa,Rodriguez-Ubis, Juan-Carlos. "Synthesis of novel macrocyclic lanthanide chelates derived from bis-pyrazolylpyridine.". . p. 213 - 216. Retrieved 2002.
• 5、 Prudencio, Miguel,Rohovec, Jan,Peters, Joop A.,Tocheva, Elitza,Boulanger, Martin J.,Murphy, Michael E. P.,Hupkes, Hermen-Jan,Kosters, Walter,Impagliazzo, Antonietta,Ubbink, Marcellus. "A caged lanthanide complex as a paramagnetic shift agent for protein NMR". . p. 3252 - 3260. Retrieved 2004.
• 6、 Yao, Weihe,Liu, Chenyu,Wang, Ning,Zhou, Hengjun,Shafiq, Farishta,Yu, Simiao,Qiao, Weihong. "O-nitrobenzyl liposomes with dual-responsive release capabilities for drug delivery". . . Retrieved 2021.
• 7、 Liu, Chenyu,Ewert,Wang, Ning,Li,Safinya, Cyrus R.,Qiao, Weihong. "A multifunctional lipid that forms contrast-agent liposomes with dual-control release capabilities for precise MRI-guided drug delivery". . . Retrieved 2019.
• 8、 Yu, Kaichao,Hamdan, Yousef,Wan, Fuxian,Li, Yinxia,Huang, Kaixun,Zhou, Jinlan. "Synthesis, relaxivity, and T1 relaxation enhancement of binuclear gadolinium(III) complexes based on DTPA or EDTA and long-chain alkyl esters of L-lysine". . p. 218 - 222. Retrieved 2007.
• 9、 Yan, Bing,Sheng, Chao,Guo, Lei. "Lanthanide (Eu3 +, Tb3 +, Gd3 +) hybrid system with functionalized diethylenetriamine pentaacetic acid: Coordination bonding assembly, luminescence and MRI contrast agent property". . p. 43 - 46. Retrieved 2012.
• 10、 Yu, Gang,Yamashita, Mitsuji,Aoshima, Kengo,Kobayashi, Masatsugu,Kato, Tatsunori,Kamikage, Nao,Takahashi, Masaki,Takayanagi, Hisao,Oshikawa, Tatsuo,Laurent, Sofie,Burtea, Carmen,Vander Elst,Muller, Robert N.,Takehara, Yasuo,Sakahara, Harumi. "Studies on preparation and characterization of novel MRI contrast agents for targeting organs and blood vessels". . p. 101 - 108. Retrieved 2007.