(2S)-1-(3,3-dimethyl-2-oxopentanoyl)pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S)-1-(3,3-dimethyl-2-oxopentanoyl)pyrrolidine-2-carboxylic acid
• CAS No.: 186268-78-0
• Molecular Formula: C12H19NO4
• Molecular Weight: 241.287
• Hs Code.: 2933990090
• European Community (EC) Number: 696-220-5
• UNII: 0709BVY57W
• Nikkaji Number: J1.264.897I
• Wikidata: Q27236238
• Metabolomics Workbench ID: 149571
• ChEMBL ID: CHEMBL4297382
• Mol file: 186268-78-0.mol

Synonyms:GM1485;GPI 1485;GPI-1485;GPI1485;NIL-A cpd;NIL-A1 cpd;NIL-A2 cpd;NIL-A3 cpd

Chemical Property of (2S)-1-(3,3-dimethyl-2-oxopentanoyl)pyrrolidine-2-carboxylic acid

Chemical Property:

• Boiling Point: 386.198 °C at 760 mmHg
• Flash Point: 187.366 °C
• PSA: 74.68000
• Density: 1.189 g/cm³
• LogP: 1.00520
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 241.13140809
• Heavy Atom Count: 17
• Complexity: 348

Purity/Quality:

99% ^*data from raw suppliers

(2S)-1-(3,3-Dimethyl-2-oxopentanoyl)-pyrrolidine-2-carboxylic acid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)(C)C(=O)C(=O)N1CCCC1C(=O)O
• Isomeric SMILES: CCC(C)(C)C(=O)C(=O)N1CCC[C@H]1C(=O)O
• Recent ClinicalTrials: NINDS Parkinson's Disease Neuroprotection Trial of CoQ10 and GPI 1485

Technology Process of (2S)-1-(3,3-dimethyl-2-oxopentanoyl)pyrrolidine-2-carboxylic acid

There total 6 articles about (2S)-1-(3,3-dimethyl-2-oxopentanoyl)pyrrolidine-2-carboxylic acid 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: 87.0%

methyl (2S)-1-(1,2-dioxo-3,3-dimethylpentyl)-2-pyrrolidinecarboxylate (186268-77-9) → (2S)-1-(1,2-dioxo-3 3-dimethylpentyl)-2-pyrrolidinecarboxylic acid (186268-78-0)

Guidance literature:

With sodium hydroxide; In methanol; at 0 - 20 ℃;

DOI:10.1021/jm010556c

Reference yield:

methyl (2S)-1-(1,2-dioxo-2-methoxyethyl)-2-pyrrolidinecarboxylate (139419-63-9) → (2S)-1-(1,2-dioxo-3 3-dimethylpentyl)-2-pyrrolidinecarboxylic acid (186268-78-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 75 percent / tetrahydrofuran / 3 h / -78 °C

2: 87 percent / aq. NaOH / methanol / 0 - 20 °C

With sodium hydroxide; In tetrahydrofuran; methanol;

DOI:10.1021/jm010556c

Reference yield:

methyl (2S)-pyrrolidine carboxylate (2577-48-2) → (2S)-1-(1,2-dioxo-3 3-dimethylpentyl)-2-pyrrolidinecarboxylic acid (186268-78-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: triethylamine / dichloromethane / 1.5 h / 0 °C

2.1: tetrahydrofuran / 3 h / -78 °C

3.1: lithium hydroxide; water / methanol / 0 - 20 °C

3.2: pH 1

With lithium hydroxide; water; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

methyl (2S)-1-(1,2-dioxo-3,3-dimethylpentyl)-2-pyrrolidinecarboxylate

methyl (2S)-1-(1,2-dioxo-2-methoxyethyl)-2-pyrrolidinecarboxylate

C₁₄H₂₃NO₄

methyl (2S)-pyrrolidine carboxylate

Downstream raw materials:

3,3-diphenyl-1-propyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-pyrrolidinecarbothioate

3-(3-pyridyl)-1-propyl (2S)-1-(3,3-dimethyl-1,2-dioxopentyl)-2-pyrrolidinecarboxylate

(S)-((R)-3-(3,4-dimethoxyphenyl)-1-(3-(2-morpholinoethoxy)phenyl)propyl) 1-(3,3-dimethyl-2-oxopentanoyl)pyrrolidine-2-carboxylate

C₁₈H₂₄N₄O₄

Refernces

• 1、 -. "Heterocyclic esters or amides for vision and memory disorders". Page/Page column 20. . Retrieved 2010/11/30.
• 2、 -. "Carboxylic acids and carboxylic acid isosteres of N-heterocyclic compounds for vision and memory disorders". Page/Page column 22-23; 25-26. . Retrieved 2008/06/13.