Dimethyl 1,1'-methylenebis(5-oxo-L-prolinate)

Base Information

• Chemical Name: Dimethyl 1,1'-methylenebis(5-oxo-L-prolinate)
• CAS No.: 77269-11-5
• Molecular Formula: C13H18 N2 O6
• Molecular Weight: 298.296
• Hs Code.: 2933790090
• European Community (EC) Number: 278-654-3
• DSSTox Substance ID: DTXSID20228002
• Nikkaji Number: J309.373E
• Wikidata: Q83107865
• Mol file: 77269-11-5.mol

Synonyms:77269-11-5;Dimethyl 1,1'-methylenebis(5-oxo-L-prolinate);EINECS 278-654-3;DIMETHYL 1,1'-METHYLENEBIS[5-OXO-L-PROLINATE];DTXSID20228002;NS00037905

Chemical Property of Dimethyl 1,1'-methylenebis(5-oxo-L-prolinate)

Chemical Property:

• PSA: 93.22000
• LogP: -0.85230
• XLogP3: -0.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 6
• Exact Mass: 298.11648630
• Heavy Atom Count: 21
• Complexity: 435

Purity/Quality:

98%Min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CCC(=O)N1CN2C(CCC2=O)C(=O)OC
• Isomeric SMILES: COC(=O)[C@@H]1CCC(=O)N1CN2[C@@H](CCC2=O)C(=O)OC

Technology Process of Dimethyl 1,1'-methylenebis(5-oxo-L-prolinate)

There total 5 articles about Dimethyl 1,1'-methylenebis(5-oxo-L-prolinate) 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: 78.0%

methanol (67-56-1) + L-(+)-1,1'-methylenebis[5-oxo-2-pyrrolidinecarboxylic acid] (16473-66-8) → L methylene bis N-(oxo-5 pyrrolidine carboxylate-2 de methyle) (77269-11-5)

Guidance literature:

With toluene-4-sulfonic acid; for 120h; Heating;

Reference yield: 46.0%

Dimethoxymethane (109-87-5) + methyl 5-oxopyrrolidine-2-carboxylate (4931-66-2,54571-66-3,64700-65-8) → N-methoxy methyl pyroglutamate de methyle (95083-43-5) + methyl methylene bis-pyroglutamate (77269-11-5)

Guidance literature:

methanesulfonic acid; for 240h; Heating;

DOI:10.1002/jhet.5570280452

Reference yield:

acide L(+)glutamique (56-86-0,617-65-2,6893-26-1,6899-05-4,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6) → L methylene bis N-(oxo-5 pyrrolidine carboxylate-2 de methyle) (77269-11-5)

Guidance literature:

Multi-step reaction with 3 steps

1: nitrobenzene / 4 h / 160 °C

2: acide paratoluene sulfonique / nitrobenzene / 0.5 h / 145 °C

3: 78 percent / p-toluenesulfonic acid / 120 h / Heating

With acide paratoluene sulfonique; toluene-4-sulfonic acid; In nitrobenzene;

upstream raw materials:

methanol

L-(+)-1,1'-methylenebis[5-oxo-2-pyrrolidinecarboxylic acid]

acide L(+)glutamique

2-L-pyrrolidone-5-carboxylic acid

Downstream raw materials:

bis(N-pyrrolidinyl)methane

Refernces

• 1、 Miquel, Christian,Pigache, Pierre,Rigo, Benoit,Kolocouris, Nicolas. "Etude dans la serie des pyrrolidinones. IV. Formation de quelques derives de l'acide L methylene bis N-(oxo-5 pyrrolidine carboxylique-2)". . p. 1447 - 1453. Retrieved 2007/10/02.