2-(2,5-Dioxopyrrolidin-1-yl)ethyl acetate

Base Information

• Chemical Name: 2-(2,5-Dioxopyrrolidin-1-yl)ethyl acetate
• CAS No.: 28833-81-0
• Deprecated CAS: 2592355-03-6
• Molecular Formula: C8H11NO4
• Molecular Weight: 185.18
• Hs Code.: 2925190090
• UNII: L7C8TC8JPX
• DSSTox Substance ID: DTXSID90556829
• Wikidata: Q82438530
• Mol file: 28833-81-0.mol

Synonyms:28833-81-0;N-acetoxyethylsuccinimide;N-Acetoxyethyl succinimide;2-(2,5-dioxopyrrolidin-1-yl)ethyl acetate;2,5-Pyrrolidinedione,1-[2-(acetyloxy)ethyl]-;L7C8TC8JPX;N-2-acetoxyethylsuccinimide;SCHEMBL3684078;DTXSID90556829;MFCD00078304;1-[2-(Acetyloxy)ethyl]-1H-pyrrole-2,5-diol;1-[2-(Acetyloxy)ethyl]-2,5-pyrrolidinedione;2,5-Pyrrolidinedione, 1-[2-(acetyloxy)ethyl]-;1H-Pyrrole-2,5-diol, 1-[2-(acetyloxy)ethyl]-

Chemical Property of 2-(2,5-Dioxopyrrolidin-1-yl)ethyl acetate

Chemical Property:

• PSA: 63.68000
• LogP: -0.36360
• XLogP3: -1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 185.06880783
• Heavy Atom Count: 13
• Complexity: 233

Purity/Quality:

99% ^*data from raw suppliers

1-[2-(acetyloxy)ethyl]-2,5-Pyrrolidinedione 97.00% ^*data from reagent suppliers

Safty Information:

• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCCN1C(=O)CCC1=O

Technology Process of 2-(2,5-Dioxopyrrolidin-1-yl)ethyl acetate

There total 5 articles about 2-(2,5-Dioxopyrrolidin-1-yl)ethyl acetate 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: 88.0%

1-(2-Hydroxy-ethyl)-pyrrolidine-2,5-dione (18190-44-8) + acetyl chloride (75-36-5) → 2-(2,5-dioxopyrrolidin-1-yl)ethyl acetate (28833-81-0)

Guidance literature:

With triethylamine; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1016/S0040-4020(01)96008-9

Reference yield: 73.0%

succinic acid anhydride (108-30-5) + ethanolamine (141-43-5) + acetic acid (64-19-7,77671-22-8) → 2-(2,5-dioxopyrrolidin-1-yl)ethyl acetate (28833-81-0)

Guidance literature:

In toluene; at 25 ℃; for 12h; Reflux;

DOI:10.1039/d1ob00754h

Reference yield:

2-methyl-4,5-dihydro-1,3-oxazole (1120-64-5,26375-28-0) + succinic acid anhydride (108-30-5) → 2-(2,5-dioxopyrrolidin-1-yl)ethyl acetate (28833-81-0)

Guidance literature:

at 175 ℃;

upstream raw materials:

2-methyl-4,5-dihydro-1,3-oxazole

succinic acid anhydride

1-(2-Hydroxy-ethyl)-pyrrolidine-2,5-dione

acetic anhydride

Downstream raw materials:

N-vinylsuccinimide

1-(2-Hydroxy-ethyl)-pyrrolidine-2,5-dione

3-(2-(1-(2-acetoxyethyl)-5-oxo-2-pyrrolidinyl)(phenylthio)acetyl)-4(R)-isopropyl-1,3-thiazolidine-2-thione

[(S)-1-(2-Methanesulfonyloxy-ethyl)-5-oxo-pyrrolidin-2-yl]-phenylsulfanyl-acetic acid methyl ester

Refernces

• 1、 Nagao, Yoshimitsu,Dai, Wei-Min,Ochiai, Masahito,Shiro, Motoo. "DIASTEREOSELECTIVE ALKYLATION OF CHIRAL TIN(II) ENOLATES ONTO CYCLIC ACYL IMINIUM IONS. ASYMMETRIC TOTAL SYNTHESIS OF (-)-SUPINIDINE". . p. 6361 - 6380. Retrieved 2007/10/02.