4-Methylene-5-oxo-L-proline methyl ester

Base Information

• Chemical Name: 4-Methylene-5-oxo-L-proline methyl ester
• CAS No.: 182073-75-2
• Molecular Formula: C₇H₉NO₃
• Molecular Weight: 155.153
• DSSTox Substance ID: DTXSID50445962
• Nikkaji Number: J746.776A
• Wikidata: Q82264514
• Mol file: 182073-75-2.mol

Synonyms:182073-75-2;4-METHYLENE-5-OXO-L-PROLINE METHYL ESTER;L-Proline, 4-methylene-5-oxo-, methyl ester (9CI);(S)-Methyl 4-methylene-5-oxopyrrolidine-2-carboxylate;methyl (2S)-4-methylidene-5-oxopyrrolidine-2-carboxylate;DTXSID50445962;(s)-(+)-methyl-4-methylene-5-oxopyrrolidine-2-carboxylate

Chemical Property of 4-Methylene-5-oxo-L-proline methyl ester

Chemical Property:

• PSA: 58.89000
• LogP: -0.12000
• XLogP3: 0.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 155.058243149
• Heavy Atom Count: 11
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C1CC(=C)C(=O)N1
• Isomeric SMILES: COC(=O)[C@@H]1CC(=C)C(=O)N1

Technology Process of 4-Methylene-5-oxo-L-proline methyl ester

There total 10 articles about 4-Methylene-5-oxo-L-proline methyl ester 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: 98.0%

methyl (+/-)-1-(2,4-dimethoxyphenyl)methyl-4-methylene-5-oxo-2-pyrrolidinecarboxylate (1201928-26-8) → methyl (+/-)-4-methylene 5-oxo-pyrrolidin-2-carboxylate (61541-27-3,182073-75-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 12h;

DOI:10.1016/j.tetasy.2009.09.009

Reference yield: 27.0%

chloro-trimethyl-silane (75-77-4) + methyl (+/-)-1-(2,4-dimethoxyphenyl)methyl-4-methylene-5-oxo-2-pyrrolidinecarboxylate (1201928-26-8) → C9H15NO3Si + (S)-(+)-methyl-4-methylene-5-oxopyrrolidine-2-carboxylate (182073-75-2)

Guidance literature:

methyl (+/-)-1-(2,4-dimethoxyphenyl)methyl-4-methylene-5-oxo-2-pyrrolidinecarboxylate; With α-chymotrypsin; at 20 ℃; for 4h; pH=7.4; aq. phosphate buffer; Resolution of racemate; Enzymatic reaction;

With hydrogenchloride; In water; pH=2;

chloro-trimethyl-silane; optical yield given as %ee; enantioselective reaction; Further stages;

DOI:10.1016/j.tetasy.2009.09.009

Reference yield: 10.0%

dimethyl (+/-)-4-methyleneglutamate hydrochloride (131320-33-7) → methyl (+/-)-4-methylene 5-oxo-pyrrolidin-2-carboxylate (61541-27-3,182073-75-2)

Guidance literature:

With ammonia; In methanol; for 4h; Reflux;

DOI:10.1016/j.tetasy.2009.09.009

upstream raw materials:

methyl (+/-)-1-(2,4-dimethoxyphenyl)methyl-4-methylene-5-oxo-2-pyrrolidinecarboxylate

dimethyl (+/-)-4-methyleneglutamate hydrochloride

methanol

(S)-5-((1S,5R,7R)-10,10-Dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]decane-4-carbonyl)-3-methylene-pyrrolidin-2-one

Downstream raw materials:

(S)-(+)-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid

(R)-(-)-4-methylene-5-oxo-pyrrolidine-2-carboxylic acid