[(3S)-1-[(4-methoxyphenyl)methyl]-2,5-dioxopyrrolidin-3-yl] acetate

Base Information

• Chemical Name: [(3S)-1-[(4-methoxyphenyl)methyl]-2,5-dioxopyrrolidin-3-yl] acetate
• CAS No.: 174874-82-9
• Molecular Formula: C14H15NO5
• Molecular Weight: 277.277
• DSSTox Substance ID: DTXSID90450595
• Nikkaji Number: J2.257.905C
• Wikidata: Q82270383
• Mol file: 174874-82-9.mol

Synonyms:CTK0E4013;174874-82-9;DTXSID90450595;1-(4-Methoxybenzyl)-3beta-acetoxypyrrolidine-2,5-dione

Chemical Property of [(3S)-1-[(4-methoxyphenyl)methyl]-2,5-dioxopyrrolidin-3-yl] acetate

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 277.09502258
• Heavy Atom Count: 20
• Complexity: 400

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OC1CC(=O)N(C1=O)CC2=CC=C(C=C2)OC
• Isomeric SMILES: CC(=O)O[C@H]1CC(=O)N(C1=O)CC2=CC=C(C=C2)OC

Technology Process of [(3S)-1-[(4-methoxyphenyl)methyl]-2,5-dioxopyrrolidin-3-yl] acetate

There total 2 articles about [(3S)-1-[(4-methoxyphenyl)methyl]-2,5-dioxopyrrolidin-3-yl] 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:

(S)-Malic acid (97-67-6,78644-42-5) + 4-methoxy-benzylamine (2393-23-9) + acetyl chloride (75-36-5) → acetic acid (3S)-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl ester (174874-82-9)

Guidance literature:

(S)-Malic acid; acetyl chloride; Reflux;

4-methoxy-benzylamine; With acetyl chloride; In dichloromethane; Reflux;

With acetyl chloride; In dichloromethane; Reflux;

DOI:10.1016/j.tetasy.2011.01.012

Reference yield:

4-methoxy-benzylamine (2393-23-9) + (S)-acetoxysuccinic anhydride (59025-03-5) → acetic acid (3S)-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl ester (174874-82-9)

Guidance literature:

With acetyl chloride; Yield given. Multistep reaction; 1.) THF, RT, 18 h, 2.) THF, reflux, 18 h;

DOI:10.1016/0040-4020(95)01085-8

Reference yield: 91.0%

acetic acid (3S)-1-(4-methoxy-benzyl)-2,5-dioxo-pyrrolidin-3-yl ester (174874-82-9) → (S)-4-hydroxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione (254730-06-8)

Guidance literature:

With ethanol; acetyl chloride; at 50 ℃; for 5h;

DOI:10.1016/S0957-4166(99)00395-X

upstream raw materials:

4-methoxy-benzylamine

(S)-acetoxysuccinic anhydride

(S)-Malic acid

acetyl chloride

Downstream raw materials:

acetic acid (2S,3S)-2-hydroxy-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-3-yl ester

(S)-4-hydroxy-1-(4-methoxybenzyl)-2,5-pyrrolidinedione

acetic acid (2S,3S)-2-acetoxy-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-3-yl ester

Acetic acid (S)-3-acetoxy-1-(4-methoxy-benzyl)-5-oxo-pyrrolidin-2-yl ester