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
• General Description: Methyl L-pyroglutamate, also known by various synonyms such as L-5-oxoproline methyl ester and (S)-5-(methoxycarbonyl)-2-pyrrolidinone, serves as a key chiral building block in organic synthesis, particularly in the enantiospecific construction of complex alkaloids like (+)-ipalbidine. Derived from L-pyroglutamic acid, it is converted into intermediates such as tosylates or olefinic amides, which are further functionalized through reactions like cuprate additions, condensations, and ozonolysis. Its utility lies in its ability to retain stereochemical integrity while enabling the formation of advanced intermediates, such as dienes or diketones, critical for intramolecular coupling reactions like McMurry couplings. This versatility underscores its importance in the synthesis of bioactive natural products and analogues.

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

Enantiospecific synthesis of an indolizidine alkaloid, (+)-ipalbidine

10.1016/S0040-4039(03)00563-X

The study details the enantiospecific total synthesis of the indolizidine alkaloid (+)-ipalbidine, a nonaddictive analgesic with additional biological activities. The synthesis starts from (?)-pyroglutamic acid and involves several key steps. Initially, the alcohol derived from pyroglutamic acid methyl ester is converted to a tosylate, which is then reacted with a higher-order cuprate reagent to form an olefinic amide. This amide is condensed with a bromide, prepared from an ester through reduction and bromination steps, to yield a diene. The diene undergoes ozonolysis to form a diketone, which is then subjected to an intramolecular McMurry coupling reaction using low-valent titanium to construct the desired carbon-carbon double bond, yielding the core structure of ipalbidine. The final steps include reduction of the amide function and debenzylation to obtain the natural product. The study also explores an alternative synthetic path involving the elimination of a vic-diol function from a major byproduct of the McMurry coupling. The developed synthetic strategy is noted for its potential applicability to the synthesis of other biologically active alkaloids.

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