Methyl 5-oxo-L-prolinate

Base Information

• Chemical Name: Methyl 5-oxo-L-prolinate
• CAS No.: 4931-66-2
• Molecular Formula: C6H9NO3
• Molecular Weight: 143.142
• Hs Code.: 29337900
• European Community (EC) Number: 225-567-3
• DSSTox Substance ID: DTXSID00197767
• Nikkaji Number: J142.923J
• Wikidata: Q72497045
• ChEMBL ID: CHEMBL4238146
• Mol file: 4931-66-2.mol

Synonyms:4931-66-2;Methyl L-pyroglutamate;Methyl (S)-(+)-2-pyrrolidone-5-carboxylate;Methyl 5-oxo-L-prolinate;L-PYROGLUTAMIC ACID METHYL ESTER;methyl (2S)-5-oxopyrrolidine-2-carboxylate;Methyl pyroglutamate;(S)-Methyl 5-oxopyrrolidine-2-carboxylate;Proline, 5-oxo-, methyl ester;L-Proline, 5-oxo-, methyl ester;EINECS 225-567-3;MFCD00080931;(+)-L-Pyroglutamic acid methyl ester;Methyl (S)-2-pyrrolidone-6-carboxylate;methyl(S)-(+)-2-pyrrolidone-5-carboxylate;H-Pyr-OMe;Methyl 5-oxo-2-pyrrolidinecarboxylate #;pyroglutamic methyl ester;Methyl (S)-Pyroglutamate;L-Pyroglutamic acid methyl;SCHEMBL78947;pyroglutamic acid methyl ester;5-Oxo-d-proline methyl ester;(S)-5-oxoproline methyl ester;CHEMBL4238146;DTXSID00197767;(L)-pyroglutamic acid methyl ester;CS-D0637;(S)-Pyroglutamic Acid Methyl Ester;BBL101837;STL555634;AKOS000280633;AKOS005145517;(S)-methyl 2-pyrrolidone-5-carboylate;(S)-5-(Methoxycarbonyl)-2-pyrrolidone;AS-38129;HY-32291;methyl (2S)-5-pyrrolidone-2-carboxylate;Methyl (S)-5-Oxopyrrolidine-2-carboxylate;(S)-methyl 5-oxo-pyrrolidine-2-carboxylate;A7376;AM20100208;M2198;methyl (S){+)-2-pyrrolidone-5-carboxylate;Methyl ester of L-Pyrrolidonecarboxylic acid;methyl(s)-(+)-2 pyrrolidone-5-carboxylate;EN300-132496;P-8580;(S)-(+)-Methyl 5-oxopyrrolidine-2-carboxylate;J-517904;Methyl (S)-(+)-2-pyrrolidone-5-carboxylate, 97%;(s)-5-oxo-pyrrolidine-2-carboxylic acid methyl ester;(S)-5-Oxopyrrolidine-2-carboxylic Acid Methyl Ester

Chemical Property of Methyl 5-oxo-L-prolinate

Chemical Property:

• Appearance/Colour: Brown oil
• Vapor Pressure: 3.64E-09mmHg at 25°C
• Refractive Index: 1.486
• Boiling Point: 304.7 °C at 760 mmHg
• PKA: 14.65±0.40(Predicted)
• Flash Point: 138.1 °C
• PSA: 55.40000
• Density: 1.204 g/cm³
• LogP: -0.23320
• Storage Temp.: Store at 0-5°C
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 143.058243149
• Heavy Atom Count: 10
• Complexity: 166

Purity/Quality:

99% ^*data from raw suppliers

Methyl(S)-Pyroglutamate ^*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: COC(=O)C1CCC(=O)N1
• Isomeric SMILES: COC(=O)[C@@H]1CCC(=O)N1
• Uses: Methyl (S)-Pyroglutamate (cas# 4931-66-2) is a compound useful in organic synthesis.

Technology Process of Methyl 5-oxo-L-prolinate

There total 53 articles about Methyl 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: 100.0%

methanol (67-56-1) + L-Pyroglutamic acid (98-79-3) → methyl (S)-pyroglutamate (4931-66-2)

Guidance literature:

With thionyl chloride; at 0 - 25 ℃;

DOI:10.1002/ejoc.201700498

Reference yield: 100.0%

methanesulfonic acid (75-75-2,98527-29-8) + L-Pyroglutamic acid (98-79-3) → methyl (S)-pyroglutamate (4931-66-2)

Guidance literature:

In methanol; chloroform; Molecular sieve; Reflux;

DOI:10.1016/j.bmcl.2020.127220

Reference yield: 100.0%

methyl (2S)-5-diazo-4-oxo-2-(2,2,2-trifluoroacetamido)-pentanoate (88668-76-2) → methyl (S)-pyroglutamate (4931-66-2)

Guidance literature:

With sodium hydrogencarbonate; In methanol; for 3h; Irradiation;

DOI:10.1039/b601097k

upstream raw materials:

methanol

D-Glutamic acid

pyroglutamoyl chloride

dimethyl N-benzylideneglutamate

Downstream raw materials:

methyl N-formylpyroglutamate

Pyroglutamic acid

N-methoxy methyl pyroglutamate de methyle

methyl methylene bis-pyroglutamate

Refernces

• 1、 Li, Jiayuan,Li, Ning,Huang, Bing,Zhao, Weihong,Wang, Wenli,Si, Yingying,Yan, Chunyan. "Biotransformation of Licochalcone A by transgenic crown galls of Panax quinquefolium". . p. 72 - 76. Retrieved 2014.
• 2、 Rapoport et al.. "-". . p. 883. Retrieved 1964.
• 3、 Aubry, Céline,Clerici, Paolo,Gerbaud, Claude,Lautru, Sylvie,Micouin, Laurent,Pernodet, Jean-Luc. "Revised Structure of Anthelvencin A and Characterization of the Anthelvencin Biosynthetic Gene Cluster". . p. 945 - 951. Retrieved 2020.
• 4、 Delany, Eoghan G.,Connon, Stephen J.. "Enantioselective N-heterocyclic carbene-catalysed intermolecular crossed benzoin condensations: Improved catalyst design and the role of in situ racemisation". supporting information. p. 248 - 258. Retrieved 2021/01/14.
• 5、 Sanchez, Clément A.,Gadais, Charlène,Chaume, Grégory,Girard, Sylvaine,Chelain, Evelyne,Brigaud, Thierry. "Enantiopure 5-CF3-Proline: Synthesis, Incorporation in Peptides, and Tuning of the Peptide Bond Geometry". supporting information. p. 382 - 387. Retrieved 2021/01/13.