2,5-Dioxopyrrolidin-1-yl methylcarbamate

Base Information

• Chemical Name: 2,5-Dioxopyrrolidin-1-yl methylcarbamate
• CAS No.: 18342-66-0
• Molecular Formula: C6H8N2O4
• Molecular Weight: 172.141
• Hs Code.: 2925190090
• European Community (EC) Number: 629-302-6
• DSSTox Substance ID: DTXSID00402666
• Nikkaji Number: J2.220.154I
• Wikidata: Q27157348
• Mol file: 18342-66-0.mol

Synonyms:18342-66-0;2,5-Dioxopyrrolidin-1-yl methylcarbamate;N-Succinimidyl N-methylcarbamate;(2,5-dioxopyrrolidin-1-yl) N-methylcarbamate;N-Succinimdyl-N-methylcarbamate;MFCD00800292;1-[(methylcarbamoyl)oxy]pyrrolidine-2,5-dione;MIC substitute;Methyl isocyanate substitute;2,5-Pyrrolidinedione, 1-[[(methylamino)carbonyl]oxy]-;N-Succinimidyl Methylcarbamate;SCHEMBL352074;CHEBI:83949;DTXSID00402666;XMNGSPOWUCNRMO-UHFFFAOYSA-N;Methylcarbamic acid succinimidyl ester;AKOS016005526;AC-4863;CS-W008138;AS-13518;SY066862;2,5-dioxopyrrolidin-1-yl N-methylcarbamate;FT-0650761;U0108;A812775;N-Succinimidyl N-methylcarbamate, >=97.0% (N);J-011744;Methyl-carbamic acid 2,5-dioxo-pyrrolidin-1-yl ester;Q27157348;N-methylcarbamic acid (2,5-dioxo-1-pyrrolidinyl) ester;[2,5-bis(oxidanylidene)pyrrolidin-1-yl] N-methylcarbamate

Chemical Property of 2,5-Dioxopyrrolidin-1-yl methylcarbamate

Chemical Property:

• Melting Point: 148-153 °C
• Refractive Index: 1.527
• PKA: 11.00±0.46(Predicted)
• PSA: 75.71000
• Density: 1.416 g/cm³
• LogP: -0.26480
• Storage Temp.: 2-8°C
• Sensitive.: Moisture Sensitive
• Solubility.: Dichloromethane (Slightly), DMSO (Slightly)
• Water Solubility.: Slightly soluble in water.
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 172.04840674
• Heavy Atom Count: 12
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

N-Succinimidyl N-Methylcarbamate ^*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: CNC(=O)ON1C(=O)CCC1=O
• Uses: N-Succinimidyl N-Methylcarbamate is used as a reagent in the synthesis of Argifin, a natural product chitinase inhibitor with chemotherapeutic potential. N-Succinimidyl N-Methylcarbamate is also used as a reagent in the preparation of 5-Amino-N1-methyl-1H-imidazole-1,4-dicarboxamide (A616300); a metabolite of Temozolomide (T017775) which is an imidazotetrazine alkylating agent and antineoplastic.

Technology Process of 2,5-Dioxopyrrolidin-1-yl methylcarbamate

There total 4 articles about 2,5-Dioxopyrrolidin-1-yl methylcarbamate 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: 86.0%

1-hydroxy-pyrrolidine-2,5-dione (6066-82-6) + methyl isocyanate (624-83-9) → 2,5-dioxopyrrolidin-1-yl methylcarbamate (18342-66-0)

Guidance literature:

With triethylamine; In ethyl acetate; at 0 - 20 ℃; for 24h;

DOI:10.1016/j.ejmech.2014.05.032

Reference yield: 80.0%

2,5-dioxopyrrolidin-1-yl carbonochloridate (15149-73-2) + methylamine hydrochloride (593-51-1) → 2,5-dioxopyrrolidin-1-yl methylcarbamate (18342-66-0)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 3 ℃; for 48h;

DOI:10.1055/s-1993-25809

Reference yield: 63.1%

di(succinimido) carbonate (74124-79-1) + methylamine (74-89-5) → 2,5-dioxopyrrolidin-1-yl methylcarbamate (18342-66-0) + N,N'-Dimethylurea (96-31-1)

Guidance literature:

In acetonitrile; Ambient temperature;

DOI:10.1016/S0040-4039(00)85958-4

upstream raw materials:

1-hydroxy-pyrrolidine-2,5-dione

methyl isocyanate

2,5-dioxopyrrolidin-1-yl carbonochloridate

methylamine hydrochloride

Downstream raw materials:

N-methyl-N-nitrosocarbamic acid N'-hydroxysuccinimide ester

cyclo(N^w-(N-methylcarbamoyl)-L-arginyl-N-methyl-L-phenylalanyl-β-L-aspartyl-β-L-aspartyl-D-alanyl)

(+/-)-Physostigmine

benzyl (3R,4R)-3-{7-bromo-3-methyl-1-[2-(3-methylureido)ethyl]-1H-indol-6-ylmethoxy}-4-{4-[3-(2-methoxybenzyl)oxypropoxy]phenyl}piperidine-1-carboxylate

Refernces

Solid-phase synthesis of cyclic peptide chitinase inhibitors: SAR of the argifin scaffold

10.1039/b815077j

The research focuses on the development of an efficient all-solid-phase synthesis method for argifin, a natural product cyclic pentapeptide chitinase inhibitor. The purpose of this study was to improve the synthesis process, overcome side reactions, and provide valuable structure-activity relationship (SAR) data for the argifin scaffold. The researchers successfully developed a new synthesis approach that avoids aspartimide formation during deprotection, using a novel aqueous acidolysis procedure. They also synthesized a series of argifin analogues based on the X-ray structure of argifin in complex with a representative family 18 chitinase, which highlighted the key role of the Arg(MC)-MePhe dipeptide in binding. The chemicals used in the process included Fmoc-protected amino acids, PyBOP/DIPEA for peptide coupling, Pd(Ph3P)4/PhSiH3 for allyl ester cleavage, and various reagents for side-chain manipulation and deprotection, such as 1H-pyrazole-1-carboxamidine hydrochloride and N-succinimidyl N-methylcarbamate. The conclusions drawn from the study emphasized the efficiency of the all-solid-phase route to argifin and its potential for automation and scale-up, as well as the importance of specific residues in the binding affinity of chitinase inhibitors.

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