2,5-dioxopyrrolidin-1-yl 5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentanoate

Base Information

• Chemical Name: 2,5-dioxopyrrolidin-1-yl 5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentanoate
• CAS No.: 103750-03-4
• Molecular Formula: C13H14 N2 O6
• Molecular Weight: 294.264
• Hs Code.: 29212900
• DSSTox Substance ID: DTXSID401153195
• Nikkaji Number: J2.771.952J
• Mol file: 103750-03-4.mol

Synonyms:103750-03-4;2,5-dioxopyrrolidin-1-yl 5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentanoate;Mal-C2-NHS ester;5-Maleimidovalericacid-NHS;5-Maleimido-pentanoic NHS ester;(2,5-dioxopyrrolidin-1-yl) 5-(2,5-dioxopyrrol-1-yl)pentanoate;5-Maleimidovaleric Acid NHS;5-Maleimidovaleric acid-NHS;5-Maleimidovaleric?acid-NHS;LCZC1197;SCHEMBL18918259;ULZJAHZPCLFGHQ-UHFFFAOYSA-N;DTXSID401153195;MFCD01318603;AKOS015909543;AS-73313;BP-24360;PD125947;HY-126502;A1875;CS-0105016;FT-0604084;EN300-103448;F82466;Z1343801315;2,5-Dioxo-3-pyrroline-1-valeric acid 2,5-dioxopyrrolizino;2,5-Dioxo-1-pyrrolidinyl 2,5-dihydro-2,5-dioxo-1H-pyrrole-1-pentanoate

Chemical Property of 2,5-dioxopyrrolidin-1-yl 5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentanoate

Chemical Property:

• PSA: 101.06000
• LogP: -0.43530
• Solubility.: Soluble in DMSO, DCM, DMF
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 294.08518617
• Heavy Atom Count: 21
• Complexity: 505

Purity/Quality:

97% ^*data from raw suppliers

2,5-Dioxopyrrolidin-1-yl5-(2,5-Dioxo-2,5-dihydro-1h-pyrrol-1-yl)pentanoate ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)OC(=O)CCCCN2C(=O)C=CC2=O
• Description: 5-Maleimido-pentanoic NHS ester contains a maleimide group and an NHS ester. The NHS ester can be used to label the primary amines (-NH2) of proteins, amine-modified oligonucleotides, and other amine-containing molecules. The maleimide group will react with a thiol group to form a covalent bond, enabling the connection of biomolecule with a thiol.

Technology Process of 2,5-dioxopyrrolidin-1-yl 5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentanoate

There total 6 articles about 2,5-dioxopyrrolidin-1-yl 5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentanoate 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: 90.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + 5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentanoic acid (57078-99-6) → 2,5-dioxopyrrolidin-1-yl 5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentanoate (103750-03-4)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 22 ℃; for 3h; Inert atmosphere;

DOI:10.1021/ml300150y

Reference yield:

t-butyl 5-(3’,6’-endoxo-A-tetrahydrophthalimido)pentanoate → 2,5-dioxopyrrolidin-1-yl 5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentanoate (103750-03-4)

Guidance literature:

Multi-step reaction with 3 steps

1: hydrogenchloride / 1,4-dioxane; water / 0.5 h / 4 °C

2: toluene; N,N-dimethyl-formamide / 6 h / Reflux

3: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane

With hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; toluene;

Reference yield:

C13H19NO4 → 2,5-dioxopyrrolidin-1-yl 5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentanoate (103750-03-4)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride / water; 1,4-dioxane / 0.5 h / 4 - 20 °C

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 20 °C

With hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane; water;

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

5-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)pentanoic acid

tert-butyl 2-hydroxyethylpropionate

Downstream raw materials:

C₄₅H₅₅F₂N₇O₁₀

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